WO2008136199A1 - Process for producing withanolide - Google Patents

Process for producing withanolide Download PDF

Info

Publication number
WO2008136199A1
WO2008136199A1 PCT/JP2008/051481 JP2008051481W WO2008136199A1 WO 2008136199 A1 WO2008136199 A1 WO 2008136199A1 JP 2008051481 W JP2008051481 W JP 2008051481W WO 2008136199 A1 WO2008136199 A1 WO 2008136199A1
Authority
WO
WIPO (PCT)
Prior art keywords
means hydrogen
producing
hydroxy
withanolide
methyl
Prior art date
Application number
PCT/JP2008/051481
Other languages
French (fr)
Japanese (ja)
Inventor
Hideo Nemoto
Yuji Matsuya
Masashi Yamada
Hiroto Suzuki
Original Assignee
Meiji Dairies Corporation
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 Meiji Dairies Corporation filed Critical Meiji Dairies Corporation
Publication of WO2008136199A1 publication Critical patent/WO2008136199A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A process for producing a compound represented by the following formula (2): (2) (wherein R1 means hydrogen, methyl, or CH2OH; R2 means hydrogen or methyl; R3 means hydrogen or hydroxy; R4 means hydrogen or hydroxy; and R5 means hydroxy, a sugar chain, or a protective group) or a salt of the compound. The process comprises subjecting a compound represented by the following formula (1): (1) (wherein R1 to R5 have the same meanings as the R1 to R5 in the formula (2)) to a cyclization metathesis reaction in the presence of a catalyst.
PCT/JP2008/051481 2007-04-26 2008-01-31 Process for producing withanolide WO2008136199A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007-117732 2007-04-26
JP2007117732A JP2010159211A (en) 2007-04-26 2007-04-26 Method for producing withanolide compounds

Publications (1)

Publication Number Publication Date
WO2008136199A1 true WO2008136199A1 (en) 2008-11-13

Family

ID=39943319

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/051481 WO2008136199A1 (en) 2007-04-26 2008-01-31 Process for producing withanolide

Country Status (2)

Country Link
JP (1) JP2010159211A (en)
WO (1) WO2008136199A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010041681A1 (en) * 2008-10-09 2010-04-15 リードケミカル株式会社 Novel sominone derivative
CN102180928A (en) * 2011-03-15 2011-09-14 中山大学 3-beta,5-alpha,6-beta-trihydroxy steroid compounds, and synthesis method and application thereof
CN114409726A (en) * 2022-01-24 2022-04-29 东华大学 Betulol cycloolefine derivative and its use and preparation method

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111001372A (en) * 2019-11-21 2020-04-14 安徽科宝生物工程有限公司 Reaction device for esterification of ursodeoxycholic acid and use method thereof

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
GAMOH K. ET AL.: "Stereocontrolled synthesis of withanolide D and related compounds", J. CHEM. SOC. PERKIN TRANS. I, 1984, pages 449 - 454 *
GHOSH A. ET AL.: "Enzymatic Acylation and Ring-Closing Olefin Metathesis: A Convenient Strategy for the Lactone Moiety of Compactin and Mevinolin", J. ORG. CHEM., vol. 65, no. 15, 2000, pages 4779 - 4781 *
PEREZ-MEDRANO A. ET AL.: "Synthesis of the highly oxygenated ergostane type steroid (+)-withanolide E", J. AM. CHEM. SOC., vol. 113, 1991, pages 1057 - 1059 *
RAMACHANDRAN P.V. ET AL.: "Stereoselective Syntheses of (+)-Goniodiol), (-)-8-Epigoniodiol, and (+)-9-Deoxygoniopypyrone via Alkoxyallylboration and Ring-Closing Metathesis", J. ORG. CHEM., vol. 67, no. 24, 2002, pages 7547 - 7550 *
WILDEMANN H. ET AL.: "A Short Olefin Metathesis-Based Route to Enantiomerically Pure Arylated Dihydropyrans and, -Unsaturated-Valero Lactones", J. ORG. CHEM., vol. 68, no. 3, 2003, pages 799 - 804, XP002433691 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010041681A1 (en) * 2008-10-09 2010-04-15 リードケミカル株式会社 Novel sominone derivative
CN102180928A (en) * 2011-03-15 2011-09-14 中山大学 3-beta,5-alpha,6-beta-trihydroxy steroid compounds, and synthesis method and application thereof
CN102180928B (en) * 2011-03-15 2013-01-16 广州市赛普特医药科技有限公司 3-beta,5-alpha,6-beta-trihydroxy steroid compounds, and synthesis method and application thereof
CN114409726A (en) * 2022-01-24 2022-04-29 东华大学 Betulol cycloolefine derivative and its use and preparation method

Also Published As

Publication number Publication date
JP2010159211A (en) 2010-07-22

Similar Documents

Publication Publication Date Title
WO2006120208A8 (en) Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein
NZ598366A (en) Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives
WO2007035629A3 (en) Process for the preparation of pyrimidinedione derivatives
MY172034A (en) Intermediate for producing bicyclic ?-amino acid derivative
UA93424C2 (en) Preparation of azoxystrobin
WO2007103105A3 (en) Processes for preparing morphinan-6-one products with low levels of alpha, beta-unsaturated ketone compounds
MX2009003257A (en) Process for synthesis of phenoxy diaminopyrimidine derivatives.
WO2008083950A3 (en) Spirocyclic tetronic acid derivatives
WO2007109810A3 (en) Methods for the preparation of imidazole-containing compounds
WO2009051387A3 (en) Process for preparation of compound containing 6a group element using reductant
UA94449C2 (en) Process for producing optically active chromene oxide compound
NZ586187A (en) Processes for the synthesis of sinomenine derivatives and their intermediate
EP1787991A4 (en) PYRROLOÝ2,3-c¨PYRIDINE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND USE
TW200738621A (en) Chemical process
WO2009066735A1 (en) Method for producing 2-azaadamantane
MY155721A (en) A process for the preparation of (3ar, 4s, 6r, 6as)-6-amino-2, 2-dimethyltetrahydro-3ah-cyclopenta[d] [1,3] dioxol-4-ol dibenzoyl-l-tartrate and to products of said process
WO2007018808A3 (en) Methods and intermediates for the synthesis of porphyrins
WO2007018807A3 (en) Methods and intermediates for the synthesis of porphyrins
WO2008136199A1 (en) Process for producing withanolide
TW200738650A (en) Process for synthesis of aryloxy diaminopyrimidines
WO2009121710A3 (en) Process for preparing nebivolol
WO2008077035A3 (en) Processes for the preparation of levetiracetam
WO2008093392A1 (en) Process for production of 2,3’-bipyridyl-6’-one
NZ589867A (en) Process for the synthesis of n-demethylated morphinane compounds
WO2008015133A3 (en) Process for preparing amidrazones

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: 08704232

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: JP

122 Ep: pct application non-entry in european phase

Ref document number: 08704232

Country of ref document: EP

Kind code of ref document: A1