WO2008003737A1 - Procédé de production de 3,3'-dihydroxyisoréniératine et ses nouveaux produits intermédiaires - Google Patents

Procédé de production de 3,3'-dihydroxyisoréniératine et ses nouveaux produits intermédiaires Download PDF

Info

Publication number
WO2008003737A1
WO2008003737A1 PCT/EP2007/056794 EP2007056794W WO2008003737A1 WO 2008003737 A1 WO2008003737 A1 WO 2008003737A1 EP 2007056794 W EP2007056794 W EP 2007056794W WO 2008003737 A1 WO2008003737 A1 WO 2008003737A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
cis
isomer
building block
phosphonium salt
Prior art date
Application number
PCT/EP2007/056794
Other languages
German (de)
English (en)
Inventor
Hansgeorg Ernst
Hagen Jaedicke
Klaus Henrich
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of WO2008003737A1 publication Critical patent/WO2008003737A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/18—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with unsaturation outside the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/10—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5456—Arylalkanephosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouveau procédé de production de 3,3'-dihydroxyisoréniératine de formule (I), ainsi que de nouveaux produits intermédiaires obtenus à partir du procédé.
PCT/EP2007/056794 2006-07-07 2007-07-05 Procédé de production de 3,3'-dihydroxyisoréniératine et ses nouveaux produits intermédiaires WO2008003737A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP06116819.1 2006-07-07
EP06116819 2006-07-07

Publications (1)

Publication Number Publication Date
WO2008003737A1 true WO2008003737A1 (fr) 2008-01-10

Family

ID=38474037

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/056794 WO2008003737A1 (fr) 2006-07-07 2007-07-05 Procédé de production de 3,3'-dihydroxyisoréniératine et ses nouveaux produits intermédiaires

Country Status (2)

Country Link
TW (1) TW200811095A (fr)
WO (1) WO2008003737A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468931A (en) * 1965-10-07 1969-09-23 Farmaceutici Italia 4'-substituted derivatives of 1,18-di(2',3',6'-trimethylphenyl-(1'))-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene
EP0005748A2 (fr) * 1978-06-02 1979-12-12 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Procédé de préparation de dérivés cyclohexéniques, ainsi que composés intermédiaires de synthèse
EP0101597A2 (fr) * 1982-08-20 1984-02-29 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Procédé pour la préparation de l'astaxanthine ainsi que les produits intermédiaires dans la synthèse de l'astaxanthine
EP0283979A2 (fr) * 1987-03-27 1988-09-28 F. Hoffmann-La Roche Ag Dérivés de l'éthinylcyclohexène
EP0882709A1 (fr) * 1997-06-04 1998-12-09 Basf Aktiengesellschaft Procédé pour la préparation de la zéaxanthine, intermédiaires pour ce procédé et procédé pour leur préparation
WO2007090095A2 (fr) * 2006-01-27 2007-08-09 Cardax Pharmaceuticals, Inc. Synthese d'analogues ou derives de carotenoides dotes de proprietes antioxydantes ameliorees

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3468931A (en) * 1965-10-07 1969-09-23 Farmaceutici Italia 4'-substituted derivatives of 1,18-di(2',3',6'-trimethylphenyl-(1'))-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene
DE1593440B1 (de) * 1965-10-07 1971-11-25 Farmaceutici Italia Substituierte 1,18-Di-[2',3',6'-trimethylphenyl-(1')]-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaene und Verfahren zu ihrer Herstellung
EP0005748A2 (fr) * 1978-06-02 1979-12-12 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Procédé de préparation de dérivés cyclohexéniques, ainsi que composés intermédiaires de synthèse
EP0101597A2 (fr) * 1982-08-20 1984-02-29 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Procédé pour la préparation de l'astaxanthine ainsi que les produits intermédiaires dans la synthèse de l'astaxanthine
EP0283979A2 (fr) * 1987-03-27 1988-09-28 F. Hoffmann-La Roche Ag Dérivés de l'éthinylcyclohexène
EP0882709A1 (fr) * 1997-06-04 1998-12-09 Basf Aktiengesellschaft Procédé pour la préparation de la zéaxanthine, intermédiaires pour ce procédé et procédé pour leur préparation
WO2007090095A2 (fr) * 2006-01-27 2007-08-09 Cardax Pharmaceuticals, Inc. Synthese d'analogues ou derives de carotenoides dotes de proprietes antioxydantes ameliorees

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TUTORSKAYA, O. O. ET AL: "Regioselective synthesis of a 2,3,5-trimethyl-p-benzoquinone monoacetal and its reactions.", XP002454244, retrieved from STN Database accession no. 1990:611886 *
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TUTORSKAYA, O. O. ET AL: "Synthesis of 4-hydroxy-2,5-cyclohexadien-1-ones with isoprenoid substituents of varying structure", XP002454243, retrieved from STN Database accession no. 1992:173610 *
M. SOUKOUP ET AL: "Technical Procedures for the Syntheses of Carotenoids and Related Compounds from 6-Oxo-isophorone:Syntheses of (3R,3'R)-Zeaxanthin", HELVETICA CHIMICA ACTA, vol. 73, no. 4, 1990, pages 868 - 873, XP002453197 *
NOBUHISA OKUKADO ET AL: "SYNTHESIS OF PHENOLIC CAROTENOID,3,3'-DIHYDROXYISORENIERATENE", MEMOIRS OF THE FACULTY OF SCIENCE SER. C, vol. 9, no. 1, 1974, XP009090156 *
O.O. TUTORSKAYA ET AL: "Regioselective Synthesis of 2,3,5-Trimethyl-p-benzoquinone monoacetal and its transformations", J.ORG.CHEM. USSR (ENGL.TRANSL.), vol. 26, no. 5, 1990, pages 936 - 940, XP009090137 *
O.O.TUTORSKAYA ET AL: "Synthesis of 4-Hydroxy-2,5-cyclohexadien-1-ones with various isoprenoid substituents", J.ORG.CHEM.USSR (ENGL. TRANS.), vol. 27, no. 7, 1991, pages 1423 - 1428, XP009090136 *
WIDMER E: "SYNTHETIC ADVANCES IN THE CAROTENOID FIELD", PURE & APPLIED CHEMISTRY, vol. 57, no. 5, 1985, pages 741 - 752, XP001063958, ISSN: 0033-4545 *
ZHURNAL ORGANICHESKOI KHIMII , 26(5), 1087-91 CODEN: ZORKAE; ISSN: 0514-7492, 1990 *
ZHURNAL ORGANICHESKOI KHIMII , 27(7), 1423-8 CODEN: ZORKAE; ISSN: 0514-7492, 1991 *

Also Published As

Publication number Publication date
TW200811095A (en) 2008-03-01

Similar Documents

Publication Publication Date Title
EP0283979B1 (fr) Dérivés de l'éthinylcyclohexène
EP0633258A1 (fr) Procédé amélioré de production d'astaxantin, nouveaux produits intermédiares et procédé de leur préparation
WO2006125530A1 (fr) Derives de tetrahydropyranne pourvus de plusieurs cycles contenant de l'oxygene et procede de production desdits derives
WO2006125550A1 (fr) Procede de production de tetrahydropyrannes a partir de tetrahydropyrann-3-ones
EP0269009B1 (fr) Procédé pour la fabrication de dérivés de carbinol
EP3556743B1 (fr) Procédé de préparation de (9e,11z)-9, 11-hexadécadiénal
US8765988B2 (en) Lycopene intermediate 1, 3, 6, 10-tetra-double bond pentadec-carbon phosphonate as well as preparation method and use thereof
Rautenstrauch Controlled allylic transformations via the meisenheimer rearrangement
US2842599A (en) Carotenoids and intermediates therefor
WO2008003737A1 (fr) Procédé de production de 3,3'-dihydroxyisoréniératine et ses nouveaux produits intermédiaires
EP0120341B1 (fr) Procédé de préparation de dérivés de pentadiénol
DE2625259A1 (de) Verfahren zur herstellung von cyclischen oxoverbindungen
EP0882709B1 (fr) Procédé pour la préparation de la zéaxanthine, intermédiaires pour ce procédé et procédé pour leur préparation
EP0919547B1 (fr) Préparation d'aldéhydes polyéniques
EP4305027A1 (fr) Synthèse et précurseurs catalytiques de cannabinol
WO2006125527A1 (fr) Procede de fabrication de derives de tetrahydropyrane
EP0814078A1 (fr) Procédé pour la préparation d'esters et d'acides polyéniques
DE60024353T2 (de) Verfahren zur Herstellung Antiosteoporicagenz
WO2008003742A1 (fr) Procédé et nouveaux produits intermédiaires permettant la production de 3,3'-dihydroxyisoréniératine
Klunder et al. Chemistry of strained polycyclic compounds—V: The stereospecific cationic cage expansion reaction of 4-homocubane carbinols to 1, 3-bishomocubane bridgehead alcohols
Botteron et al. Ring-Size Effects in the Pinacol Rearrangement
US4224253A (en) Novel bicyclic scents
EP0131130B1 (fr) Procédé de préparation de cycloalcènylalcynes
US2849495A (en) Preparation of 3, 4-dehydro-beta-carotene
DE602004009544T2 (de) Neue 3,3-Dimethyl-5-Cyano-Benzoxepinderivate verwendbar zur Herstellung von 5-Formyl-Benzoxepinderivaten

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07787089

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

NENP Non-entry into the national phase

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 07787089

Country of ref document: EP

Kind code of ref document: A1