JPS56123932A - Preparation of 4-hydroxycyclopentenone - Google Patents

Preparation of 4-hydroxycyclopentenone

Info

Publication number
JPS56123932A
JPS56123932A JP2730280A JP2730280A JPS56123932A JP S56123932 A JPS56123932 A JP S56123932A JP 2730280 A JP2730280 A JP 2730280A JP 2730280 A JP2730280 A JP 2730280A JP S56123932 A JPS56123932 A JP S56123932A
Authority
JP
Japan
Prior art keywords
optically active
dihydroxyl
binaphthyl
lialh
organic solvent
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.)
Granted
Application number
JP2730280A
Other languages
Japanese (ja)
Other versions
JPS6234025B2 (en
Inventor
Ryoji Noyori
Mugio Nishizawa
Seiji Kurozumi
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.)
Teijin Ltd
Original Assignee
Teijin Ltd
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 Teijin Ltd filed Critical Teijin Ltd
Priority to JP2730280A priority Critical patent/JPS56123932A/en
Publication of JPS56123932A publication Critical patent/JPS56123932A/en
Publication of JPS6234025B2 publication Critical patent/JPS6234025B2/ja
Granted legal-status Critical Current

Links

Classifications

    • 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

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

PURPOSE: To obtain the titled optically active substance, by the reduction of a cyclopentene-3,5-dioden with LiAlH4 in an inert organic solvent in the presence of an optically active 2,2'-dihydroxyl-1,1'-binaphthyl and a lower aliphatic alcohol.
CONSTITUTION: One mole of a compound expressed by formula I is reduced with an equimolar amount of LiAlH4 in an inert organic solvent in the presence of an optically active 2,2'-dihydroxyl-1,1'-binaphthyl in an equimolar amount and a 1W 4C aliphatic alcohol in an amount of 1W1.2mol at -100W0°C for several minutes to one hour, and if necessary, the hydroxyl group is protected to give a compound expressed by formula II (R is H or a protecting group; *is an asymmetric carbon).
EFFECT: The aimed substance may be given effectively in high optical yield from a readily available raw material.
USE: An intermediate for the preparation of a variety of medicines, e.g. prostaglandin or maytansine having a carcinostatic effect.
COPYRIGHT: (C)1981,JPO&Japio
JP2730280A 1980-03-06 1980-03-06 Preparation of 4-hydroxycyclopentenone Granted JPS56123932A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2730280A JPS56123932A (en) 1980-03-06 1980-03-06 Preparation of 4-hydroxycyclopentenone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2730280A JPS56123932A (en) 1980-03-06 1980-03-06 Preparation of 4-hydroxycyclopentenone

Publications (2)

Publication Number Publication Date
JPS56123932A true JPS56123932A (en) 1981-09-29
JPS6234025B2 JPS6234025B2 (en) 1987-07-24

Family

ID=12217288

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2730280A Granted JPS56123932A (en) 1980-03-06 1980-03-06 Preparation of 4-hydroxycyclopentenone

Country Status (1)

Country Link
JP (1) JPS56123932A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59144729A (en) * 1983-02-03 1984-08-18 Sumitomo Chem Co Ltd Preparation of optically active 4-hydroxy-2- cyclopentenones
JPS6064943A (en) * 1983-08-10 1985-04-13 Sumitomo Chem Co Ltd Production of optically active 4-hydroxycyclopentenone
JPS60132927A (en) * 1983-12-21 1985-07-16 Sumitomo Chem Co Ltd Optically active cyclopentenone and production thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59144729A (en) * 1983-02-03 1984-08-18 Sumitomo Chem Co Ltd Preparation of optically active 4-hydroxy-2- cyclopentenones
JPS6064943A (en) * 1983-08-10 1985-04-13 Sumitomo Chem Co Ltd Production of optically active 4-hydroxycyclopentenone
JPS60132927A (en) * 1983-12-21 1985-07-16 Sumitomo Chem Co Ltd Optically active cyclopentenone and production thereof

Also Published As

Publication number Publication date
JPS6234025B2 (en) 1987-07-24

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