Preparation of Chiral, Highly Functionalized Cyclopentanes and Its Application to the Synthesis of Prostaglandin E1

Kouji OKANO; Hiroshi SUEMUNE; Kiyoshi SAKAI

doi:10.1248/cpb.37.1995

Preparation of Chiral, Highly Functionalized Cyclopentanes and Its Application to the Synthesis of Prostaglandin E₁

Kouji OKANO, Hiroshi SUEMUNE, Kiyoshi SAKAI

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Keywords: prostaglandin E₁, air-oxidation, microbial reduction, chemoselective oxidation, stereoselective reduction

JOURNAL FREE ACCESS

1989 Volume 37 Issue 8 Pages 1995-1998

DOI https://doi.org/10.1248/cpb.37.1995

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Abstract

This paper describes the preparation of the polyfunctionalized cyclopentane ((±)-5) by silica gel-catalyzed air-oxidation, and its kinetic resolution by means of microbial reduction with Rhodotorula rubta to afford optically pure (-)-5 (>99% ee). Starting with (-)-5, a new route to prostaglandin E₁ was established.

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