PROSTAGLANDIN INTERMEDIATE AND ITS PRODUCTION

PROSTAGLANDIN INTERMEDIATE AND ITS PRODUCTION

PROBLEM TO BE SOLVED: To obtain a new 2-oxa-bicyclo[3,3,0]octan-3-one derivative useful as an intermediate for synthesizing prostaglandins of high optical purity, by reaction of a specific cyclopentanol derivative with a condensation agent. SOLUTION: The objective compound of formula II e.g. (1S,5R,...

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Bibliographische Detailangaben
Hauptverfasser: NOIDE MANABU, INOUE TAKEHISA
Format: Patent
Sprache:eng
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Zusammenfassung:PROBLEM TO BE SOLVED: To obtain a new 2-oxa-bicyclo[3,3,0]octan-3-one derivative useful as an intermediate for synthesizing prostaglandins of high optical purity, by reaction of a specific cyclopentanol derivative with a condensation agent. SOLUTION: The objective compound of formula II e.g. (1S,5R,6R,7R)-(-)-2- oxa-6-(methoxycarbonyl-7-acetoxybicyclo[3,3,0]octan-3-one} is obtained by reaction of (A) a compound of formula I (R and R are each a 1-6C alkyl) [e.g. (1R,2R,3R,4R)-2-(methoxycarbonylmethyl)-3-(methoxycarbonyl)-4- acetoxycyclopentanol] with (B) a condensation agent in an organic solvent such as benzene at 10-180 deg.C (esp. 70-90 deg.C).