Preparation of bicyclo 3.3.0 octane derivative

Abstract

Abstract PURPOSE: To prepare the titled compound useful as a synthetic intermediate of 9(O)-methanoprostacycline, etc., in a shortened production process, by the condensation reaction of diformylmethylcyclopentane derivative in the presence of a base or a base and a metal salt. CONSTITUTION: The objective compound of formula II such as 3α-hydroxy-4β- formvl-7-oxobicyclo[3.3.0]octane, etc. is prepared by the condensation reaction of the compound of formula I (A is oxo or carbonyl-protecting group) such as 1-oxo- 3α,4α-diformyl-methylcyclopentane in a solvent such as acetonitrile in the presence of a base such as pyridine hydrochloride or a combination of the base and a metal salt such as zinc acetate, in an inert gas tream (e.g. N 2 ) at -10°C W about room temp. for 30minW10hr. The amount of by-product can be reduced by using a metal salt in combination with the base. USE: A synthetic intermediate of 9(O)methanoprostacycline or its derivative effective as a remedy and preventive for thermobosis. COPYRIGHT: (C)1982,JPO&Japio

Inventors

• 👤 Shigeo Amamiya
• 👤 Koichi Kojima
• 👤 Kiyoshi Sakai

Bibliographic Details