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WO2008012108A3 - Process for the preparation of polyhydroxylated stilbenes via claisen condensation - Google Patents

Process for the preparation of polyhydroxylated stilbenes via claisen condensation Download PDF

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Publication number
WO2008012108A3
WO2008012108A3 PCT/EP2007/006726 EP2007006726W WO2008012108A3 WO 2008012108 A3 WO2008012108 A3 WO 2008012108A3 EP 2007006726 W EP2007006726 W EP 2007006726W WO 2008012108 A3 WO2008012108 A3 WO 2008012108A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
claisen condensation
polyhydroxylated
stilbenes
via claisen
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2007/006726
Other languages
French (fr)
Other versions
WO2008012108A2 (en
Inventor
Jonathan William Wiffen
Raymond Mccague
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bial Portela and Cia SA
Original Assignee
Bial Portela and Cia SA
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
Priority claimed from EP06015770A external-priority patent/EP1884508A1/en
Application filed by Bial Portela and Cia SA filed Critical Bial Portela and Cia SA
Publication of WO2008012108A2 publication Critical patent/WO2008012108A2/en
Publication of WO2008012108A3 publication Critical patent/WO2008012108A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a process for the preparation of polyhydroxylated stilbenes starting from a compound of the formula (I) formula (VI) or formula (IX).
PCT/EP2007/006726 2006-07-28 2007-07-30 Process for the preparation of polyhydroxylated stilbenes via claisen condensation Ceased WO2008012108A2 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
EP06015772 2006-07-28
EP06015772.4 2006-07-28
EP06015773 2006-07-28
EP06015773.2 2006-07-28
EP06015770.8 2006-07-28
EP06015770A EP1884508A1 (en) 2006-07-28 2006-07-28 Process for the preparation of polyhydroxylated stilbenes via claisen condensation

Publications (2)

Publication Number Publication Date
WO2008012108A2 WO2008012108A2 (en) 2008-01-31
WO2008012108A3 true WO2008012108A3 (en) 2008-05-22

Family

ID=38872461

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/006726 Ceased WO2008012108A2 (en) 2006-07-28 2007-07-30 Process for the preparation of polyhydroxylated stilbenes via claisen condensation

Country Status (1)

Country Link
WO (1) WO2008012108A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109970517B (en) * 2019-04-28 2021-09-17 杭州师范大学 Preparation method of resveratrol compound

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005069998A2 (en) 2004-01-20 2005-08-04 Brigham Young University Technology Transfer Office Novel sirtuin activating compounds and methods for making the same
FR2904311B1 (en) * 2006-07-28 2013-01-11 Clariant Specialty Fine Chem F NEW PROCESS FOR THE SYNTHESIS OF (E) STILBENIC DERIVATIVES PERM TO OBTAIN RESVERATROL AND PICEATANNOL
WO2010046926A2 (en) * 2008-10-17 2010-04-29 Aptuit Laurus Pvt Ltd Novel stilbene analogs
ES2663746T3 (en) * 2011-12-01 2018-04-16 Laurus Labs Limited  Process for the preparation of polyhydroxystilbene compounds by deprotection of the corresponding ethers
CN104151232A (en) * 2014-06-30 2014-11-19 北京万全德众医药生物技术有限公司 Method for preparing etocoxib
CN111686817B (en) * 2019-03-14 2024-02-09 上海博腾智拓医药科技有限公司 Copper-supported catalyst, preparation method and application thereof
CN114195610B (en) * 2022-01-05 2023-07-14 海南大学 A kind of synthetic method of E-type internal olefin compound
CN120864958A (en) * 2025-09-26 2025-10-31 浙江六康生物科技有限公司 A continuous flow preparation method for benzenemod, hydrogenated benzenemod and their analogues

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CARDILE V ET AL: "Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues", BIOORGANIC CHEMISTRY, ACADEMIC PRESS INC., NEW YORK, NY, US, vol. 33, no. 1, February 2005 (2005-02-01), pages 22 - 33, XP004720666, ISSN: 0045-2068 *
G. VIJAY B. REDDY ET AL: "CLEAVAGE OF NONPHENOLIC BETA-1 DIARYLPROPANE LIGNIN MODEL DIMERS BY MANGANESE PEROXIDASE FROM PHANEROCHAETE CHRYSOSPORIUM", EUROPEAN JOURNAL OF BIOCHEMISTRY , 270(2), 284-292, vol. 270, no. 2, 2003, pages 284 - 292, XP002415071 *
ROBERTS ET AL: "THE PHOTOCHEMISTRY OF 1-(3,5-DIMETHOXYPHENYL)-2-(4-METHOXYPHENYL)ETHYL ETHANOATE IN ALCOHOL SOLVENTS: A SEARCH FOR CARBOCATION REARRANGEMENTS", CANADIAN JOURNAL OF CHEMISTRY, NATIONAL RESEARCH COUNCIL. OTTAWA, CA, vol. 81, no. 6, 2003, pages 709 - 722, XP009076767, ISSN: 0008-4042 *
TALVITIE ET AL: "ENRICHMENT, CHARACTERIZATION AND ABSOLUTE CONFIGURATION OF THE ENANTIOMERS OF 1-(3,5-DIMETHOXYPHENYL)-2-(4-METHOXYPHENYL)ETHANOL", ACTA CHEMICA SCANDINAVICA, MUNKSGAARD, COPENHAGEN, DK, vol. 50, no. 12, 1996, pages 1143 - 1146, XP009076763, ISSN: 0904-213X *
ZHANG ET AL: "SYNTHESIS OF RESVERATROL AND RESVERATROL TRINICOTINATE", JOURNAL OF CHINESE PHARMACEUTICAL SCIENCES, SCHOOL OF PHARMACEUTICAL SCIENCES, BEIJING MEDICAL UNIVERSITY,, CN, vol. 13, no. 1, 2004, pages 10 - 13, XP001248789, ISSN: 1003-1057 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109970517B (en) * 2019-04-28 2021-09-17 杭州师范大学 Preparation method of resveratrol compound

Also Published As

Publication number Publication date
WO2008012108A2 (en) 2008-01-31

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