JPH058710B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION (Technical Field of the Invention) The present invention relates to a novel anti-1,3-polyol compound and a method for synthesizing the same. (Background of the Invention) In recent years, in connection with research on the synthesis of physiologically active natural products containing 1,3-polyols, such as ionophores, polyenes, and polyoxomacrolide antibiotics, research on the synthesis of 1,3-polyols has been conducted. is being actively carried out. The present inventors previously developed a stereoselective synthesis method for syn-1,3-polyol system (A) (T.
Nakata, et al Tetra hedron Letters, 24 ,
3873 (1983)). Therefore, if it is possible to synthesize the anti-1,3-polyol system (B), which is a stereoisomer of the syn-1,3-polyol system, the synthesis of the above-mentioned physiologically active natural products will be extremely easy. It becomes easier. (Objective of the Invention) An object of the present invention is to provide a novel anti-1,3-polyol compound that can be used as a fragment compound of an ionophore, a polyene, and a polyoxomacrolide antibiotic. Another object of the present invention is to provide a new method for synthesizing the above-mentioned anti-1,3-polyol compounds, which have been difficult to synthesize. (Structure of the Invention) <Synthesis of Starting Material> The starting material (1) of the present invention can be obtained from -malic acid, for example, by the following process. (S.Haneshian and P.Lavellee, J.Org.Chem.,
48, 4427 (1983)). <Synthesis of target compound> Starting material (1) is reacted with lithium diisopropylamine (LDA) and CH ₃ COO ^t Bu to obtain β-hydroxy ester (2). A suitable solvent is tetrahydrofuran (THF). The appropriate reaction temperature and reaction time are -40 to -78°C and 0.5 to 5 hours, respectively. The obtained β-hydroxy ester (2) is oxidized to obtain β-keto ester (3). Suitable oxidizing agents include John's reagent-acetone, pyridinium chlorochromate-dichloromethane, and pyridinium dichromate-dichloromethane. The reaction temperature and reaction time were 0°C to room temperature and 1 to 12°C, respectively.
The time is appropriate. The obtained β-ketoester (3) is treated with a dithiol and a Lewis acid to obtain a lactone (4). As the Lewis acid, BF ₃ -ether and aluminum chloride are suitable. Further, suitable solvents include methylene chloride and dichloroethane. The reaction temperature and reaction time are 0°C to room temperature, respectively.
12 to 72 hours is appropriate. The obtained lactone was dissolved in ^t BuPh ₂ SiC in the presence of a base.
React with to obtain silyllactone (4'). For example, imidazole is suitable as the base. Further, dimethylformamide (DMF) is suitable as a solvent. The reaction temperature may be room temperature, and the reaction time may be 3 to 30 minutes.
6 hours is appropriate. The obtained silyllactone (4′) was treated with LDA and
React with CH ₃ COO ^t Bu to obtain hemiacetal (5). The reaction conditions are the above β-hydroxyester (2)
The reaction conditions are the same as for obtaining . The obtained hemiacetal (5) is reacted with orthoformate and camphorsulfonic acid to obtain acetal (6). Suitable solvents include methanol-methylene chloride, methanol, and the like. The reaction temperature may be room temperature, and the reaction time is 0.5
~3 hours is appropriate. The obtained acetal (6) is dedithiolated to obtain the ketone (7). The dedithiolating agent is N-bromsuccinimide (NBS) _-AgNO3 / _CH3CN -water,
CuC ₂ /CuO/acetone and the like are preferably used.
In the former case, the reaction conditions are preferably 0°C and 15 minutes to 1 hour, and in the latter case, refluxing for 1 to 3 hours is suitable. The obtained ketone (7) is desilylated and demethanolated to obtain enone (8). This reaction is n-
By using Bu ₄ NF, this can be done all at once. The reaction temperature may be room temperature, and the reaction time may be 1 to 3
The time is appropriate. The obtained enone (8) is treated with an acid to obtain the ketoacetal (9). The acid used is preferably camphorsulfonic acid, toluenesulfonic acid, trimethylsilylsulfuric acid, or the like. Reaction temperature and reaction time are room temperature to 60℃, respectively.
So, 12 to 120 hours is appropriate. The obtained ketoacetal (9) is stereoselectively reduced to obtain alcohol (10). As the reducing agent, K-selectride [[formula]] and L-selectride [[formula]] are suitable. The reaction temperature and reaction time were -40 to 78℃, respectively.
20 minutes to 3 hours is appropriate. The obtained alcohol (10) is treated with dithiol and Lewis acid to obtain β-thioacetal-δ-lactone (11). As the Lewis acid, BF ₃ -ether and aluminum chloride are suitable. Suitable solvents include methylene chloride and dichloromethane. The reaction temperature and reaction time were -50 to 0°C, respectively.
1 to 6 hours is appropriate. The obtained β-thioacetal-δ-lactone (11) is reacted with acetone dimethyl acetal and camphorsulfonic acid to obtain acetonide (12). The reaction temperature may be room temperature, and the reaction time is 30 minutes to 2
The time is appropriate. The obtained acetonide (12) is reduced to obtain lactol (13). Suitable reducing agents include diisobutylaluminum hydride, triethoxylithium aluminum hydride, and the like. Suitable solvents include toluene, xylene, ether, and the like. The reaction temperature and reaction time were -78℃ to 0, respectively.
°C for 0.5 to 5 hours is appropriate. The obtained lactol (13) was treated in the presence of a base,
Reaction with BrCH ₂ OCH ₃ gives methoxymethyl ether (14). As a base, diisopropylethylamine,
Dimethylaniline is preferred. This reaction is 12
Perform reflux for ~24 hours. The obtained methoxymethyl ether (14) is dedithiolated to obtain methoxymethyl ether-ketone (15). The reaction conditions are the same as described above. The resulting methoxymethyl ether-ketone (15) is reduced to give isopropylidene-alcohol (16). As reducing agents, LiAH ₄ , LiBH ₄ , NaBH ₄
is used, and suitable solvents include ether, tetrahydrofuran, methanol, etc. The reaction temperature and reaction time are from room temperature to −20°C, respectively.
°C for 0.5 to 3 hours is appropriate. Obtained isopropylidene-alcohol (16)
is reacted with dithiol and Lewis acid to obtain polyol (17). As the Lewis acid, BF ₃ -ether and aluminum chloride are suitable. The reaction temperature is approximately 0°C, and the reaction time is approximately 0.5 to 3 hours. The obtained polyol (17) is prepared by a conventional method, for example,
Acetylation is performed with acetic anhydride-pyridine to obtain an acetyl compound. Thus, according to the present invention, anti-1,3-polyol compounds can be obtained stereoselectively and in high yield. An example of the process of the present invention is as follows. Next, the present invention will be explained in more detail with reference to Examples. Example 1 Diisopropylamine at 0°C under argon flow
0.86ml of anhydrous tetrahydrofuran in 7ml solution
3.93 ml of 1.47N-BuLi-hexane solution was added dropwise and stirred for 30 minutes. Then, 0.82 ml of CH ₃ COO ^t Bu was added dropwise at -78°C, and after stirring at the same temperature for 30 minutes, ~417 mg of aldehyde (1) was added.
7 ml of anhydrous tetrahydrofuran solution was added dropwise, and 1
Stir for hours. After the reaction, add saturated NaHCO ₃ aqueous solution, return to room temperature, extract with ether, and saturate the ether layer.
After washing with NaHCO ₃ aqueous solution and saturated saline, MgSO ₄
It was dried. When the solvent was distilled off, ~664 mg of β-hydroxy ester (2) was obtained. This was directly subjected to the next reaction. Example 2 Pyridinium chlorochromate 24.09g and 3A
- Molecular sieves powder 19g methylene chloride
~11.64g of β-hydroxy ester (2) in 200ml solution
Add 50 ml of methylene chloride solution and leave at room temperature for 2 hours.
The mixture was stirred for a minute. After the reaction, ether was added and subjected to florisil column chromatography, β-ketoester (3) ~
8.51g was obtained. [Physical properties of (3)] NMR (CDC ₃ ): δ 1.35, 1.41 (s respectively;
2×Me) 1.47 (s; ^t Bu) 3.39, 3.40 (d, J=15.5Hz, respectively; COC H
₂ COO ^t Bu) 3.57 (dd, J = 8.5, 6.6 Hz; C _{1 -} Ha) 4.16 (dd, J = 8.5, 6.1 Hz; C _{1 -} Hb) 4.47 (m; C _{2 -} H) Example 3 β - Add 2 ml of 1,2-ethanedithiol to 304 mg of ketoester (3), and then BF ₃ · Et ₂ at 0°C.
0.3 ml of O was added, and the mixture was stirred at room temperature for 1.5 hours. After evaporating the solvent under reduced pressure, 2 ml of dimethylformamide, 1.5 g of imidazole, and 0.9 ml of ^tBuPh ₂ SiC were added to the residue, and the mixture was stirred at room temperature.
After 30 minutes, 1.5 g of imidazole and 0.9 ml of ^tBuPh ₂ SiC were added, and after 3 hours, 0.3 ml of ^tBuPh ₂ SiC was added. After 4 hours, water was added and extracted with ether. The ether layer was washed with saturated brine and dried over MgSO ₄ . After evaporation of the solvent, lactone (4) is subjected to a silica gel flash column (hexane:ether = 3:2).
345mg was obtained. [Physical properties of (4)] NMR (CDC ₃ ): δ 1.08 (s, ^t Bu) 2.97 (d, J = 17.6 Hz; C ₅ -H) 3.18 (dd, J = 17.6, 2.5 Hz; C ₅ 〓-H) 4.57 (m; C ₂ 〓-H) IR (neat): 1745cm ^-1 [α] ²⁸ _D +8.1° (C = 1.33, CHC ₃ ) Example 4 At 0°C under an argon stream diisopropylamine
1 in 3 ml of 134μ anhydrous tetrahydrofuran solution.
553μ of 6N-BuLi-hexane solution was added dropwise and stirred for 30 minutes. Then, 127μ of CH ₃ COO ^t Bu was added dropwise at −78° C., and the mixture was stirred at the same temperature for 45 minutes. A solution of 145 mg of lactone (4) in 2 ml of anhydrous tetrahydrofuran was then added dropwise and stirred for 15 minutes. After the reaction, 2 ml of saturated ZnC ₂ -ether solution was added, and after 5 minutes, saturated NaHCO ₃ aqueous solution was added and the temperature was returned to room temperature, followed by ether extraction. The ether layer was washed with saturated brine and then dried with MgSO ₄ . After distilling off the solvent, the residue was subjected to silica gel column chromatography (hexane:ether=3:1) to obtain 169 mg of hemiacetal (5). [Physical properties of (5)] NMR (CDC ₃ ): δ 1.04, 1.41 (each s; 2
× ^t Bu) 2.12 (dd, J=13.7, 2.0Hz; C ₅ 〓−H) 2.38 (dd, J=13.7, 2.0Hz; C ₅ 〓−H) 2.50 (s; C ₇ −H ₂ ) 5.29 ( d; J = 2.0 Hz; OH) IR (neat): 3440, 1725 (sh), 1710 cm ^-1 [α] ²⁵ _D +6.1° (C = 1.03, CHC ₃ ) Example 5 Hemiacetal (5) 1.740 Methyl orthoformate in 14 ml of methylene chloride-methanol (1:1) solution of
8.7 ml and 16 mg of camphorsulfonic acid were added, and the mixture was stirred at room temperature for 4 hours. After the reaction, add ether, saturated NaHCO ₃ aqueous solution,
After washing with saturated brine, it was dried with MgSO ₄ . After distilling off the solvent, the residue was subjected to silica gel flash column chromatography (hexane:ether=4:1) to obtain 1.385 g of acetal (6) . [Physical properties of (6)] NMR (CDC ₃ ): δ 1.05, 1.44 (respectively s; 2 × ^t Bu) 2.46, 2.66 (respectively d, J =
13.8Hz; C ₇ − H ₂ ) 2.49 (d, J = 14.2 Hz, C ₅ 〓 − H) 2.50 (dd, J = 14.2, 1.5 Hz; C ₅ 〓 − H) 3.24 (s; OMe) IR (neat ): 1730cm ^-1 [α] ²⁵ _D +18.3° (C = 1.27, CHC ₃ ) Example 6 5ml of an aqueous solution of 815mg of sodium carbonate was added to a solution of 2.61g of silver nitrate in 20ml of acetonitrile, stirred at room temperature for 15 minutes, and then heated to 0°C. N-bromosuccinimide
2.49g was added and stirred at the same temperature for 5 minutes. Furthermore, a solution of 1.375 g of acetal (6) in 8 ml of acetonitrile and 2 ml of water were added at 0° C. and stirred for 20 minutes. After the reaction, add 9 ml of saturated aqueous Na ₂ SO ₃ solution and 50 ml of methylene chloride-hexane (1:1) and return to room temperature.
Passed through Celite, methylene chloride-hexane (1:
1) After washing the solution with ether, saturate the organic layer
_NaHCO3 aqueous solution, washed with saturated saline, _MgSO4
It was dried. After distilling off the solvent, silica gel column chromatography (hexane:ether = 2:1) yielded ketone (7).
1.113g was obtained. [Physical properties of (7)] NMR (CDC ₃ ): 1.06, 1.45 (s respectively;
2× ^t Bu) 2.39, 2.41 (d, J = 14.8 Hz, respectively; C ₇ − H ₂ ) 3.23 (s; OMe) IR (neat): 1725 cm ^-1 [α] ²⁶ _D +22.0° (C = 1.30 , CHC ₃ ) Example 7 30 mg of ketone (7) in 1.5 ml of anhydrous tetrahydrofuran
Add 40 mg of n-Bu ₄ NF・3H ₂ O to the solution and leave at room temperature 1.5
Stir for hours. After the reaction, the solvent was distilled off and subjected to preparative thin layer chromatography (ether) to obtain 10.7 mg of enone (8). [Physical properties of (8)] NMR (CDC ₃ ): 1.47 (s; ^t Bu) 3.22, 3.24 (d, J = 16.4 Hz, respectively; C ₇ − H ₂ )
5.42 (s; C ₅ −H) IR (neat): 3420, 1730, 1665, 1615 cm ^-1 [α] ²⁶ _D +116.7° (C = 1.04, CHC ₃ ) Example 8 Chloride of 150 mg of enone (8) 40 mg of camphorsulfonic acid was added to 8 ml of methylene solution, and the mixture was stirred at room temperature for 66 hours. After the reaction, the methylene chloride layer was washed with a saturated aqueous solution of NaHCO ₃ and then dried with MgSO ₄ . After distilling off the solvent, the residue was subjected to silica gel column chromatography (ether:hexane=2:1, ether, ethyl acetate) to obtain 72.3 mg of acetal (9). [Physical properties of (9)] NMR (CDC ₃ ): δ 1.47 (s; ^t Bu) 2.84 (d, J = 16.6 Hz; C ₅ -H) 3.86 (d, J = 7.3 Hz; C _{1 eodp} - H) 4.89 (td, J = 4.9, 1.5 Hz; C ₂ -H) IR (neat): 1725 cm ^-1 [α] ²⁵ _D -28.6° (c = 0.8, CHC ₃ ) Example 9 Under argon flow, K-Selectride was added to a solution of 68.9 mg of ketone (9) in 3 ml of anhydrous tetrahydrofuran at -78°C.
0.43 ml (1M tetrahydrofuran solution) was added dropwise and stirred at the same temperature for 30 minutes. After the reaction, add 0.7 ml of water, return to room temperature, extract with ether, wash the ether layer with saturated saline,
Dry with _MgSO4 . After distilling off the solvent, silica gel column chromatography (ether) yields alcohol (10).
56.9mg was obtained. [Physical properties of (10)] NMR (CDC ₃ ): δ 1.47 (s; ^t Bu) 2.16 (dd, J = 14.8, 4.8 Hz; C ₅ -H) 4.07 (m, W1/2 = 10 Hz; C ₄ 〓-H) 4.61 (m, W1/2 = 10Hz; C ₂ -H) IR (neat): 3480, 1730cm ^-1 [α] ²⁵ _D -31.6° (c = 0.8, CHC ₃ ) Example 10 Under an argon stream, 1 ml of 1,3-propanedithiol and 0.4 ml of BF ₃ Et ₂ O were added dropwise to a solution of 53 mg of alcohol (10) in 3 ml of methylene chloride at -50 to -
Stir at 35° for 1.5 hours. After the reaction, the solvent was distilled off under reduced pressure and the residue was subjected to silica gel preparative thin layer chromatography to obtain 58 mg of lactone (11). [Physical properties of (11)] NMR (CDC ₃ ): 2.94 (d, J = 17.1Hz; C ₇ 〓
−H) 3.20 (dd, J=17.1, 2.0Hz; C ₇ 〓−H) 4.94 (m, W1/2=29Hz; C ₄ 〓−H) Example 11 A solution of 716 mg of lactone (11) in 40 ml of methylene chloride 18 ml of acetone dimethyl acetal and 100 mg of camphorsulfonic acid were added, and the mixture was stirred at room temperature for 30 minutes. After the reaction, add saturated NaHCO ₃ aqueous solution, extract with ether, and wash the ether layer with saturated saline.
Dry with _MgSO4 . After distilling off the solvent, the residue was applied to a silica gel flash column (ethyl acetate:hexane=1:1) to obtain 646.6 mg of acetonide (12). [Physical properties of (12)] NMR (CDC ₃ ): δ 1.36, 1.41 (each s, 2
×Me) 2.97 (d, J=17.1Hz; C ₇ 〓−H) 3.20 (dd, J=17.1, 1.7Hz; C ₇ 〓−H) 4.37 (m; C ₂ −H) 4.82 (m; C ₄ 〓-H) IR (neat): 1730cm ^-1 [α] ¹⁹ _D -32.1° (C = 1.48, CHC ₃ ) Example 12 Lactone (12) 82mg at -78℃ under argon stream
0.3 ml of isobutylaluminum hydride (25 g/100 ml hexane solution) was added dropwise to 6 ml of anhydrous toluene solution and stirred for 1 hour. After the reaction, add 0.18 ml of isopropanol, return to room temperature, then add 0.11 ml of K, stir, and add ether.
MgSO ₄ and silica gel were added and filtered, and the liquid was distilled off and subjected to silica gel column chromatography (ether:hexane=4:1) to obtain 69.5 mg of lactol (13). From NMR, this is β-OH form: α-OH form≒>
The 4:1 mixture was directly subjected to the next reaction. Example 13 A solution of 7.8 mg of lactol (13) in 1.5 ml of methylene chloride in 0.3 ml of diisopropylethylamine _BrCH2
0.1 mg of OCH ₃ was added and the mixture was refluxed for 20 hours. After the reaction, saturated NaHCO ₃ aqueous solution was added, ether extraction was performed, and the ether layer was washed with saturated NaHCO ₃ aqueous solution and saturated brine, and then dried over MgSO ₄ . After distilling off the solvent, silica gel preparative thin layer chromatography (ether:
8.7 mg of methoxymethyl ether (14) was obtained. [Physical properties of (14)] NMR (CDC ₃ ): δ 1.35, 1.40 (s; 2×Me, respectively) 2.48 (dt, J=13.4, 2.0Hz; C ₇ 〓−H) 3.41 (s; OMe) 4.01 (m; C ₄ 〓-H) 4.62, 4.97 (d, J = 6.6Hz, respectively; -OCH ₂
O-) 5.05 (dd, J=9.5, 2.0Hz; C ₈ 〓-H) Example 14 A solution of 200 mg of silver nitrate in 3.2 ml of acetonitrile was added to a solution of 62 mg of Na ₂ CO ₃ in 0.8 ml of water, stirred at room temperature for 15 minutes, and then stirred at room temperature for 15 minutes. 190 mg of N-bromosuccinimide was added at °C and stirred for 5 minutes, and a solution of 65 mg of thioacetal (14) in 1.5 ml of acetonitrile and 0.2 ml of water were added and stirred for 20 minutes. After the reaction, 0.7 ml of a saturated aqueous Na ₂ SO ₃ solution and a methylene chloride-hexane (1:1) solution were added, filtered through Celite, washed with ether, and the organic layer was washed with a saturated aqueous NaHCO ₃ solution and dried over MgSO ₄ . After evaporation of the solvent, 39 mg of ketone (15) was obtained. [Physical properties of (15)] NMR (CDC ₃ ): δ 1.35, 1.40 (s; 2×Me, respectively) 2.52 (dd, J=15.0, 8.9Hz; C ₇ 〓−H) 2.66 (ddd, J= 15.0, 2.8, 1.7Hz; C ₇ 〓-H) 3.40 (s; OMe) 3.84 (m; C ₄ 〓-H) 4.64, 5.04 (d, J = 6.8Hz, respectively; -OCH ₂
O−) 4.98 (dd, J=8.9, 2.8Hz; C ₈ 〓−H) IR (neat): 1725 cm ⁻¹ Example 15 0 in a suspension of 15 mg of LiAH ₄ in 2 ml of anhydrous ether
A solution of 32 mg of ketone (15) in 2 ml of anhydrous ether was added dropwise at °C, and the mixture was stirred for 30 minutes. After reaction, add 15μ of water, 15μ of 15% NaOH aqueous solution,
45μ of water was successively added, and then ether and MgSO ₄ were added and filtered. After distilling off the liquid, silica gel flash column chromatography (ether, ether: ethyl acetate = 2:
1), 32.5 mg of alcohol (16) was obtained. [Physical properties of (16)] NMR (CDC ₃ ): δ 1.35, 1.40 (s; 2×Me, respectively) 1.56 (s; C ₆ −OH) 3.41 (s; OMe) 3.55 (m; C ₄ 〓− H) 3.88 (m; W1/2=25Hz; C ₆ 〓-H) 4.60, 5.00 (d, J=6.6Hz, respectively; -OCH ₂
O-) 4.70 (dd, J = 9.8, 2.2 Hz; C ₈ 〓-H) IR (neat): 3420 cm _-1 Example 16 A solution of 24.9 mg of alcohol (16) in 5 ml of methylene chloride was heated at 0°C under an argon stream. Then, 0.5 ml of 1,3-propanedithiol and 0.3 ml of BF ₃ ·Et ₂ O were added dropwise, and the mixture was stirred at the same temperature for 1 hour. After distilling off the solvent, silica gel preparative thin layer chromatography (methylene chloride: methanol =
10:1) yielded 15 mg of alcohol (17). Then alcohol (17) 14mg pyridine 1.3ml
0.1 ml of acetic anhydride was added to the solution and left at room temperature for 12 hours. After the reaction, the solvent was distilled off and subjected to silica gel preparative thin layer chromatography (ethyl acetate:hexane = 1:1).
7 mg of acetyl compound (18) and 9.6 mg of diacetyl compound were obtained. 9.6mg of diacetyl compound was re-acetylated,
(18) 10.5 mg was obtained. A total of 17.5 mg of acetyl form (18) was obtained. [Physical properties of (18)] NMR (CDC ₃ ): δ 2.026, 2.047, 2.059, 2.071 (s; 4 × Ac, respectively) 4.01 (dd, J = 12.0, 5.6Hz; C ₁ −Ha) 4.03 (dd , J = 7.6, 6.3Hz; C ₈ -H) 4.25 (dd, J = 12.0, 3.7Hz; C ₁ -Hb) IR (neat): 1735, 1240cm _-1 [α] ²² _D -5.2° (C = 1.09， _CHC3 ）

Claims (1)

[Claims] 1 (In the formula, R represents a hydrogen atom or an acetyl group.) An anti-1,3-polyol compound represented by the following. 2. The compound according to claim 1, wherein R is a hydrogen atom. 3. The compound according to claim 1, wherein R is an acetyl group. 4 formula: (Me represents a methyl group.) The compound represented by the formula is treated with lithium diisopropylamine and CH ₃ COO (t-C ₄ H ₉ ) and then oxidized to give the formula: ( ^tBu represents a t-butyl group, and Me is the same as above) A compound represented by the formula is obtained, and the compound is reacted with ethanedithiol in the presence of a Lewis acid to form the formula: A compound represented by is obtained, and the compound is converted into ^t BuPh ₂ SiC
(tert-butyl diphenylsilyl chloride), formula: ( ^t Bu is the same as above, Ph represents a phenyl group.) A compound represented by the following is obtained, and the compound is reacted with lithium diisopropylamine and CH ₃ COO (t-C ₄ H ₉ ) to form the formula: ( ^t Bu, Ph are the same as above.) A compound represented by the following was obtained, and the compound was reacted with camphorsulfonic acid and CH(OCH ₃ ) ₃ to form the formula: ( ^t Bu, Ph, Me are the same as above.) A compound represented by the following was obtained, and the compound was dedithiolated to form the formula: ( ^t Bu, Ph, Me are the same as above.) Obtain the compound represented by (n-C ₄ H ₉ )
₄ Reacted with NF, formula: ( ^tBu is the same as above) A compound represented by is obtained, and the compound is treated with an acid,
formula: ( ^t Bu is the same as above.) Obtain the compound represented by, reduce the compound,
formula: ( ^t Bu is the same as above.) A compound represented by the formula is obtained, and the compound is reacted with propanedithiol in the presence of a Lewis acid to form the formula: A compound represented by is obtained, the compound is reacted with acetone dimethyl acetal and camphorsulfonic acid, and then reduced to give the formula: (Me is the same as above) was obtained, and the compound was converted into BrCH ₂ OCH ₃
React with the formula: (Me is the same as above) A compound represented by the formula is obtained, and the compound is dedithiolated to form the formula: (Me is the same as above) A compound represented by is obtained, and the compound is reduced,
formula: (Me is the same as above) A compound represented by the formula is obtained, and the compound is reacted with propanedithiol in the presence of a Lewis acid to form the formula: A compound represented by is obtained, and the compound is acetylated to form the formula: (Ac represents an acetyl group) A method for synthesizing an anti-1,3-polyol compound, characterized by obtaining a compound represented by the following.