JPS5913747A - Cis-bicyclo(3,3,0)octane compound and its preparation - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (R1 is H or lower alkyl; R2 and R3 are H, lower alkyl, aryl, etc.; E is lower alkylene, A and B are H or protecting group; the steric configuration of the bond denoted by the wavy line is alpha or beta). EXAMPLE:3alpha-( 4'-Methoxycarbonylbutyl )-7alpha-t-butyldimethylsilyloxy-8beta-( 3alpha'-t-butyl-dimethylsilyloxy-trans-1'-octenyl)-cis-bicyclo[3,3,0]- octan-2-one. USE:It has blood platelet coagulation inhibiting and gastric juice secretion suppressing activities, and is useful for the treatment and prevention of cardiac infarction, prevention and remedy of postoperative thrombosis, and prevention and remedy of peptic ulcer. PROCESS:The compound of formula I can be prepared by reducing the carbonyl group of the novel ketone compound of formula II to hydroxyl group, and when A and B are protecting groups, optionally eliminating the groups by hydrolysis.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides derostanicline analogues and their products 1@
It is about law.

More specifically, the present invention relates to the general formula [1] [wherein R is a hydrogen atom or a lower alkyl group, and R
2 and R3 are the same or different and are a hydrogen atom, a lower alkyl group, an aryl group, or a group that together form a saturated carbon ring, E is a lower alkylene group, and A and B are The same or different hydrogen atoms or optionally different protecting groups are represented, and the linear bond in the formula represents either the α configuration or the β configuration. The present invention relates to a novel /subi/chloro[:L3,0]octane compound represented by the following formula and a method for producing the same.

The compound Kr (1) represented by the general formula [1] has two asymmetric carbon atoms (2), so theoretically four stereoisomers of Id exist. Namely, 2α-3α, 2α-3β, 2
There are four pr isomers: β-3α and 2β-3β. The present invention provides a new compound and four isomers of 1 and 1, and when it is necessary to produce these isomers as a mixture, for example, when it is desired to separate and produce 3α and 3β compounds, If you want to produce only 2α-3α, or if you want to produce only 2α-3β, any stereoisomer can be produced as needed, which is impossible with conventional technology. The present invention provides a method for manufacturing.

In the compound represented by the general formula [J], examples of the lower alkyl group for Rl include C1 to C4 alkyl groups such as methyl, ethyl, n-propyl, inglovir, r1-butyl, and R2 and R3 Examples of lower argyl groups include methyl, ethyl, n-propyl, inof0
Examples of aryl groups include C7 or higher alkyl groups such as lobil, r]-butyl, inobutyl, [1-"l'y-thyl, ino-/tyl, and n-hexyl. Examples of aryl groups include phenyl, substituted Examples of groups in which R and R2 together form a diluted carbocycle include tetramethyl, naphthyl, chenyl, substituted chel, etc.
, -Onotamethylene, etc., or alkylene in the form of a branch technique. As an example of the lower alkylene group of E, 1 is C? such as methylene, ethylene, trimethylene, tetramethylene, etc. List the alkylene chains of ~C. Protective groups represented by A and B include lower alkanoyl groups such as acetyl and probionyl, as well as benzoyl,
Aroyl groups such as substituted benozoyl, be7-nor groups, tetrahydroviranyl, tetrahydrofuryl, (Cl-C4) alkoxy/methyl, and / such as trimethyl/lyl, butylnomethyl/lyl, 1,-butylnophenylrunlyl groups, etc. This includes the commonly used hydroxyl protecting groups of lyle ethers.

In the compound represented by the nfTM formula [1], where R is a hydrogen atom, the carboxylic acid can be converted into a pharmacologically acceptable salt form as necessary. . Examples of the salts include salts of metals such as sodium, potassium, magnenium, carunium, aluminum, and primary and 2nd class,
Mention may be made of tertiary and quaternary ammonium salts.

Prostacyclin has a strong inhibitory effect on platelet aggregation, suppresses gastric acid secretion, and lowers blood pressure, and although it is expected to prevent and treat various diseases, it is chemically unstable and has various physiological activities. On the contrary, the current situation is that there are still issues to be solved in order to commercialize it as a drug with a specific purpose. Therefore, the emergence of stable and physiologically active isolated m-linked compounds is in high demand.

The present invention is a chemically stable compound having the entire structure with a 70-stacyl structure and other stable analogues, such as 6α-mono-((-16β-9(o)-notano-POI).
? Useful as an intermediate for producing general formula [1]
The present invention provides a novel 3,3,o1 octane compound represented by the following formula and its method. As a result of pharmacological tests, the compound according to the present invention has a significant inhibitory effect on platelet 1 aggregation and gastric juice secretion [7. The compound represented by the general formula [1], which has been found to be a useful drug for the prevention and treatment of gastric ulcers, can be produced according to the route shown in the reaction formula below.
Ru.

[In the formula, R]. +R2+R3+E. +A, B, and wavy line combinations have the same meanings as above. ] The above first step is carried out by selectively hydrogenating only the double bonds of the αβ unsaturated bonds of the compound represented by the general formula [4] having two or more than two carbon-carbon double bonds. This is a step for producing the compound [3]. Various methods can be applied to this reduction reaction by hydrogenation, and an effective method for bamboo includes a method of reducing the bamboo using hydrogen gas in the presence of a catalytic catalyst.

Examples of the catalyst for this merging include catalysts used in general hydrogenation reactions such as platinum, paranoum, ronium, nickel, and cobalt. Further, this reaction can preferably be carried out in an inert solvent such as methanol, ethanol, inoprogol, etc., but any solvent can be used as long as it does not interfere with this reaction. Regarding the reaction humidity and hydrogen pressure at this time, either heating and pressurizing conditions or normal temperature and normal pressure conditions may be used, but when selectively hydrogenating only the desired double hydrogen gas, It is preferable to perform the injection with cooling and pressure.

The second step is a step of producing a compound represented by general formula [1] by reducing the carbinyl group of the compound represented by general formula [3] obtained as described above.

Examples of redeeming agents used in this step include various metal hydrides, preferably sodium and d-hydrides.
There are many reducing agents that can selectively reduce only carbonyl compounds such as hydride, L,-Selectrite (manufactured by Aldrinch).

This reaction is carried out in an inert solvent, and examples of the solvent include methanol, ethanol, benzene, THF, noethyl ether, etc., but any conditions that do not interfere with this reaction are selected.

Mapζ, the compound produced by this reaction has stereoisomers derived from the hydroxyl group in the structure, but by selecting the reduction conditions described in -L, it is possible to obtain only the α-coordinated hydroxyl group. It is possible. Any reaction temperature can be selected from -78°C to room temperature.

The third step is a step of producing a new compound represented by the general formula CI'l. That is, this process is performed using the general formula [
This is a method in which the compound represented by [3] is isomerized into a new compound represented by the more thermodynamically stable general formula [2], and then the carbonyl group is reduced. The conditions for this isomerization include solvents that are inert to this reaction, such as aromatic hydrocarbons such as benzene/toluene, lower alcohols such as methanol, ethanol, and impropanol, or noethyl ether, tetrahydrofuran, etc. Examples of common ether colors include:

In carrying out the isomerization described above, the isomerization reagents to be used are sodium methoxide, potassium methoxide, and potassium methane.
Examples include alkali metal salts of lower alcohols, such as sodium ethoxylate, sodium ethoxylate, potassium ethoxylate, and sodium inoderocolyte, or alkali metal salts. 10 times the amount can be used. This isomerization reaction proceeds satisfactorily in a heated state or at room temperature, and a compound represented by the general formula [2] is produced. Through this isomerization reaction, a mixture of the compound represented by the general formula [2] and the core compound represented by the general formula [3] is obtained. It is possible to separate only the compound represented by general formula [2]. As a result of various studies on the above-mentioned:Iv source conditions, the present inventors found that
The compound represented by the general formula [3] is used in a mixture state without separation, and only the compound represented by the general formula [2] is used in 1! I developed a method to do this. That is, the method involves: cooling to around -78°C in an inert solvent;
It is characterized by treatment with excess sodium borohydride. By this method, only the compound represented by the general formula [2] can be reduced. Examples of the inert cetosolvent in this case include those used when reducing the compound represented by general formula [3] in the second step and the solvents exemplified as L7.

When the reduction reaction described in 2 is carried out at room temperature, the compound represented by the one-pronged formula [C3] is also reduced, so if a mixture of the compound of the general formula [2] and the compound of the general formula [3] is reduced in this way, A mixture of four A-forms represented by the general formula [l] is obtained.

In the above method according to the present invention, the necessary stereoisomer is selected from among the four stereoisomers represented by the general formula [1] by selecting the conditions. It is characterized by the fact that it is possible to do so, and it provides a novel means that can accomplish objectives that cannot be accomplished using conventional techniques.

The compound represented by the general formula [1] according to the present invention is a useful compound that exhibits useful physiological activity such as a pre-fertility and can contribute to medical society.

Examples of the present invention are shown below, but these are specific examples and the present invention is not limited to these in any way.

Actual case 13α-(4'-methoxy/carbonylbutyl)-
7α-t-butylnomethyl 7lyluoquine-8β-(3'
α-Mo-butylnomethylsilyloki/mono-trans-1'
-Production of octenyl)one-binkku [3,3,0]octan-2-one.

3-(4'-Methoquinecarbonylbutylidene)-7α-t-butylnomethylrinriruoki/-8→β-(3'α-
t-butylnomethyl/riluoki/-trans-17-octenyl)/subi/ku0[3,3,0]octane-2
-ono was dissolved in anhydrous methanol solution, 10% Pd-C was added to the square width/l, and the catalyst was stirred for 7 hours using hydrogen gas at 1 atm while cooling at T-3 (+'C).Then, the catalyst was IP-treated. After evaporation, methanol was distilled off under reduced pressure, and the residue was subjected to gel column color chromatography.The title compound was obtained in a yield of 1) and 2.

IF{l′max. 1740,1460,]360,1
255.1080,835,775 NMRδ (CDCI-3): 5.44 (2H, m), 3
．． 90-4.20 (2H, m), 3.65 (3H, S)
, 2.30(21{,t)MASS(m/e):608
(M+), 593,577,551(1,f'-tBu
) 453 Example 22α-Hydroxy/-3α-(4′-171・quinryluponylbutyl)-7α-mo=butylnomethyl/liruoquine-8β-(3′α-mo-butylnomethylnliluoquine-trans-1′ -octenyl)nsubicycloC
3.3.0] octane, and 2β-hydroquine-3α-
(4'-methoxycarbonylbutyl)-7α-butylnomethyl/riluoki/-8β-(3'α-t-butylnomethyl/riluoki/-trans=1'-octenyl)
Production of octane.

The anhydrous methanol solution of the compound obtained in Example 1 was cooled to 0"G for 1 hour, sodium borohydride was added for 4 hours, and the tank was stirred. After confirming the disappearance of the raw materials, a saturated diet [burned water was added in excess The reducing agent is decomposed 1, and then extracted with ether.The extracted layer is washed with saturated brine, dried over anhydrous magnesium sulfate, and the ether is distilled off under reduced pressure. 1. Purification by graphie. The title compound was obtained in a yield of 97%. (Production ratio of about 2.6:1) film 2αOH form IR 3550 (sh), 3450, 174
0, maχ 1460,1250,835,775 NMFtδ (CDCt3): 5.42 (2H, m), 3
．． 81-4.1.0 (3H, m), 3.65 (3H, s
), 3.37(].}], d, J=ToIlz%D20
) MASS (m/e): 610 (M+'), 592, 55
3(M+-tBu)2βOH body IRvf11m: 345
0,1740,1460,+255,+11aX 835,775 NM}{δ(CI)CA3):5.48(2H,m),
3.5~4.2(:uhH,m), 3.66(3[{,s
) MASS (m/e'): 610 (M+), 59F+, 5
92,553 (M+-tBu) Actual example 32α-hydroxy/-3α-(4'-methoxy/cald?nylbutyl)-7
α-Mo-butynolenomethylsilyloxy-8β-(3'
α-t-butyrnomethyl/riluoki/monotrans-1'
-Production of octenyl)nsubicyclo[3.3.0')octane.

An anhydrous tetrahydrofuran solution of the compound obtained in Example 1 was cooled to -78°C, and then 1.2 equivalents of L-selectride (manufactured by Aldrich) was added and stirred for 2 hours. Then, saturated brine was added thereto and extracted with ether. After drying the ether layer over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was purified using Nori-Gel Column Chroma 1/Graphie to obtain the title compound in a yield of 70%. This item is ゛rLC, IR, NMR
and the results measured by MASS were completely consistent with the data for one of the compounds obtained in Example 2.

Example 42 α-Hydroquine-3β-(4'-,7'-/-trans-17- Production of octenyl)/subinculo[3,3.0]octano.

The ketone compound obtained in Example 1 was dissolved in pure 7K methanol, and a methanol solution containing 0.1 equivalent of sodium, notkind was added thereto, and the mixture was stirred at room temperature for 15 hours. The mixture was then cooled to -78°C, 10 times the molar amount of sodium borohydride was added, and the mixture was stirred for 24 hours. At the same temperature, saturated brine was added to quench the reaction. Then,
This was extracted with ether, the extracted layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica glucolumn chromatography. (yields are shown minus the raw materials recovered).

f'jl. nl IRνm8x3550(Sh)l3450,1740,
1460,13601250,835,775 NMRδ(cr)ct. ): 5.52 (2H, m), 4
．． 10(1}1,m), :{60~3.90(2H,m
'), 3.67 (3H, s), 2,35 (2H, t,,
J=7. (1) MΔSS (m/e): 610 (M+), PIF13,5
35,478.46+,421.329 Actual example 52β-hydroxy-3β-(4'-methquinecarbonylbutyl)-7α--=butylnomethylnriluoquine-8β-(3'α-t-butyl Dimethyl 7lyloquine-trans-17-octenyl)-bi/chloro[
3,3.0'] Manufacture of Octano.

The compound obtained in Example 1 was dissolved in anhydrous methanol, and 0.
A methanol solution containing 1 equivalent of sodium methoxide was added, and the mixture was stirred at room temperature for 15 hours. Then, to this, 4
After adding an equivalent amount of sodium borohydride and stirring for 4 hours, saturated brine was added and extracted with ether. After drying the extract over anhydrous magnesium marrow acid, the solvent is distilled off and the residue is subjected to silica gel column chromatography. i!
# When prepared, the same compound as shown in Example 2 and Practical Example 4 and the title compound were obtained.

IRv”m: 345 (1,1740,1460.136
(1.1250max NMRδ (cDct3): 5.53 (2H.m), 2.
65(3H,s)Example 62α-hydroquino-;3β-
(4'-methoxy/carvinylbutyl)-7α~t-butylnomethylnriruoquino-8β-(3'α-t-butyldimethylnriruoqui/monotora/su-1'-octenyl)
/Manufacture of soubincro[3,3.0]octane.

3β-(4'-methoxy/car-nylbutyl)-7α-t
~butyldimethylniruloki/-8β-(3'α-t-
butylnomethyl/riluoki/1trans-1'-octenyl)/subi/kuuchi C3.3.0'] octane-2-
Cool the methanol solution of Ono to -78°C, add 1
After adding 0 times the mole of sodium borohydride and stirring for 24 hours, saturated brine was added at the same temperature to stop the reaction.

After the reaction was stopped, the title compound was obtained by the same treatment as described in Example 4.

IR. The results of instrumental analyzes such as NltlR and MASS are truly terrifying. They were the same as those obtained in Example 4.

Procedural amendment (method) July 79, 1939 Kazuo Wakasugi, Commissioner of the Japan Patent Office 1. Indication of the incident 1932 Patent Application No./2/33'l 2 Name of the Invention [3,. 3.0] Octane compound and its manufacturing method 3 Related to the case of the person making the amendment Patent applicant Address: No. 1, 2g, Kamijujo λ-chome, Kita-ku, Tokyo Name: Ota Pharmaceutical Co., Ltd. 4. Agent address: 3-chome, Kojimachi, Chiyoda-ku, Tokyo, Lambda, Mutual Daiichi Building, Kamewa (626 left) 96g9 Name (7yu70) Minami Takao Φ网5. Date of amendment order: July 7, 1980 (Date of dispatch: λ Otsu, July 1970) 6. Specification subject to amendment (/~/0 page, /left page)7. Reprint of the statement of contents of the amendment (pages /~/0, pages /k) (no change in content) Description 1. Title of the invention Cis-bicyclo C3,3.01 octane compound and method for producing the same 2 Claims 1) General formula [wherein, Rti atom or lower alkyl,
R, A & R 3 digits rise at the same time, water bean atom, low da l
Alkyl, aryl, or both together form a saturated carbocyclic ring, EVi is lower alkylene, and A and B are the same or are the same or different atoms. In the formula, the wave MM combination represents either the α configuration or the β configuration. , 2) General formula [In the formula, R, hydrogen atom, low alkyl, or illusion, R
, and B, are the same or different and are a 7k atom, a lower atom or an aryl group, or both together form a carbocyclic ring, and E is a lower alkylene group. A and B are the same or different and represent a rice atom or a safety group which may be different {7, the wavy bond in the formula represents either the α configuration or the β configuration. ] per K to form a new cis-bicyclo(3.3.0') octane compound represented by the general formula [where Rl,
Rp. Rl-LA+F' and the combination of wave m have the same meaning as in the previous period. ] By converting this h into a water beak by converting it into a new one-ton carpinil expressed by 1, it becomes necessary to IF; In some cases, A. A method for producing the above-mentioned cis-bicyclo(3,3.01-octane compound), which comprises removing R and R by hydrolysis.

3) General formula [In the formula, R? is a hydrogen atom or a lower alkyl group, R
2 and B are the same or in turn are an atom atom, a lower alkyl group, or an aryl group, or both are trapped together to form a degraded carbon f. E is a low-strength alkylene group, A and B are the same or different and represent a hydrogen atom or a hydrogen atom, which may be a combination, and the wave section in the formula is α Represents one of the three-dimensional west side of the stomach. ] Expressed as a new cis-bisic mouth [3, 3.01 octane compound in 1 liter! In issuing the I Order, the general formula [wherein R
1+horse, R! ItE+A and B represent the same baby taste f as above. ] A new ketone compound represented by the general formula [where Rl! RttR! ! ．． E, A and B represent the same tones as above. ] A novel ketone compound represented by is synthesized, and then its carbinyl is converted into a hydroxyl group by impersonation; ．． Removal of Fl and R1 by hydrolysis -t
Pre-Era Sisubicyclo with Rokoto as a special monk [3, 3.0]
Method for preparing octane compounds.

4) General formula [In the formula, R1 is a hydrogen atom or a lower alkyl group, and R
, and R. t and t hold the same stratum, and are a hydrogen atom, a lower alkyl group, and an aryl, or both together form a ψ carbon, and E is a lower alkylene dust. Yes, A and B are the same boundary and water'P. I<
A new cis-bicyclo [ :>, 3.01 When producing an octane compound, a momentary formula [where R1!
RIl+R3+EIA and B have the same meanings as above. ] A dinone compound represented by the general formula [in the formula, R], P2, R3+F. ．． A and B represent the same meaning as 17 snore. ] to produce a new ketone compound represented by 1, and then to sit in a water-drunk state by holding the cardenyl in one's arms.
Depending on the need, A. A novel method for producing cis-bicyclo[3.3,n]octane compounds, which is characterized in that any T of B and R1 is removed by adding 7kf+-.

5) General formula [In the formula, B1 is a hydrogen atom or lower alkyl, and R
J and R are the same or together are a water atom, a lower alkyl group, or an aryl, or both together form a carbon macrocycle; It is an alkylene group, and A and B may be the same or Via may be a water atom or 1-t different. (g"represents either.) When producing a new cis-bisic compound [3,3.01 octanized compound], a one-kill formula [in the formula, R1.R
I1+"5+E+A and B represent the same meanings as above.

] The enone compound represented by the following is catalytically reduced to give the general formula [wherein R]+Rl! lR! ITE, A and r): Bu has the same meaning as above. ] gI′r+8. A ketonized compound is produced, and then the ketone compound of the upper period is produced by an isomerization reaction, with the general formula [wherein R)+Rp+R3+EyA and B have the same meanings as in the previous step. ] After converting into a new ketone compound represented by
If necessary, the above-mentioned cis-bicyclo[3. :{． (1) Enamel production method for octane compounds.

3. Detailed explanation of the invention Invented by prostacyclin proboscis and its tR
This is related to the J construction method.For more details, wood inventions in general [1] [In the formula, R1 is a hydrogen atom or a low alkyl group, and R
2 and R5 are the same or different and are a hydrogen atom, a certain lower alkyl group, or an aryl group, or both together form a saturated carbon group, E is a lower alkylene group, and A and B are the same or different and represent a hydrogen atom or a divalent group which may be different f'i, and the linear bond in the formula is α-stand [wherein, R1+R2+R3+E+A+B, the wavy bond represents the same meaning as above. ] The first right of the above is a general compound that is produced by selectively hydrogenating only the double bonds of the αβ unsaturated bonds of the compound represented by the general formula [4] having 2 @ or 2 or more carbon-carbon double bonds. This is the process for preparing the compound of formula [3]. This hydrogenation

Claims (1)

[Claims] 1) General formula [wherein, B is a hydrogen atom or a lower alkyl group, and R
2 and R3 are the same (or different) and are a hydrogen atom, a lower alkyl group, or an aryl group, or a group that together forms a saturated carbon ring, and is an Efi lower alkylene group, and A and B are the same or different and represent hydrogen atoms or optionally different protective groups, and the wavy bond in the formula is α
Represents either the configuration or the β configuration. ] An octane compound represented by /Subi/ChloC3,3.0]. 2) General formula [In the formula, R1 is a hydrogen atom or a lower alkyl group, and R
, and R1 are the same or different and are a hydrogen atom, a lower alkyl group, or an aryl group, or a group in which the two are taken together to form a saturated carbon ring, E is a lower alkylene group, and A and B are the same or different and represent a protecting group, which may be the same or different, and the conjugate in the formula represents either the α-configuration or the β-configuration. ] A novel cis-vinchro C. 3,3.0] In producing the octane compound, the general formula [wherein, Rl+
R2+R. 3+E+AIB and the dashed line combination have the same meanings as above. ] In 1 to 4, A and B are protecting groups as necessary. Nakiai (A, B and R1
A method for producing the above-mentioned /Subi7O[3,3,0]octane compound, which focuses on removing any arbitrary group of 'In moisture. 3) General formula [wherein, R1 is a hydrogen atom or a lower alkyl group, R
2 and R3 are the same or different and are a hydrogen atom, a lower alkyl group, an aryl group, or a group together forming a saturated bromine ring, E is a lower alkylene group, and A and B are the same or different and represent a hydrogen atom or a certain protection which may be different; Ppaα
It represents either the configuration or the 1dβ configuration. ] In order to prepare a new/Subinclo C3,3.01 octane compound represented by the general formula [where R1+R
p, +'R3+E+A and B represent the same meanings as above. ] A new ketone compound represented by the general formula [where R? IR2+R3+E+A and B represent the same meanings as above. ] A novel ketono compound represented by A. A method for producing the cis-bicycloC3,3.0']octane compound, characterized in that arbitrary groups of B and R1 are removed by hydrolysis. 4) General formula [wherein, R1 is a hydrogen atom or a lower alkyl group, R
2 and R3 are the same or different and are a hydrogen atom, a lower alkyl group, an a, aryl group, or both together form a saturated carbon ring, E is a lower alkylene group, and A and B is the same or different hydrogen atom or rri
1 represents a protective group that may be the same or different, and the wavy bond in the formula represents either the α-configuration or the β-configuration. ] In producing a new nsubi/chloro[3,3,o]octano compound represented by the general formula [wherein R y + .
R2+R3+F, , A and B represent the same meaning as in AiJ. ] The enone compound represented by the formula is catalytically reduced, and the general formula [wherein ■{, , R21R31EIA and B are ili!
i'. and expresses the same meaning as the old one. ] to produce a new ketone compound, and then convert the cardenyl group into a hydroxyl group by decoding the cardenyl group,
A novel/subi7 chloro[3,3.0]octane compound characterized in that, if necessary, when A and B are protecting groups, arbitrary groups of A, B and R1 are removed by hydrolysis. Palanquin method. 5) General formula [In the formula, R? is a hydrogen atom or a lower alkyl group, R
2 and R3 are the same or different, and are a hydrogen atom, a lower alkyl group, or an aryl group, or both together form a sulfated carbon ring, E is a lower alkyl 7 group, and A and B represent a hydrogen atom or a protecting group which may be the same or different, and the wavy bond in the formula represents either the α configuration or the β configuration. ] In molding the octane ratio compound represented by New/Subi/CroC3,3.0, the general formula [where R, R
2. Formulas E, A and B have the same meanings as above. ] A non-compound represented by the following is catalytically reduced to give the general formula [wherein R]'R2+R3+E+A and B have the same meanings as above. ] that does not generate a new ketone compound represented by
The upper ketono compound is prepared by the isomerization reaction using the general formula [wherein RElR21R31El'A and B represent the same meaning as @Konji. ] After converting into a new ketone compound represented by
and a method for producing the above-mentioned /Subi/CroC3,3.0]okuku/compound ζross, characterized in that any group of R1 is removed by hydrolysis.