Synthetic Approaches to Naturally Occurring Cyclopentanes

Abstract

PART I. Five synthetic routes to the prostaglandins, a group of highly substituted cyclopentanes, have been explored. The first four routes were unsuccessful but have provided interesting and useful information on a variety of substituted cyclopentanes. The fifth route has resulted in the isolation of 2-(6-cyanohexyl)-3-(oct-l-yn-3-ol) cyclopent-2-enone. The transformation of this important intermediate into the prostaglandin structure requires three further structural changes - the hydrolysis of the nitrile group, the selective reduction of the enyne system to a trans double bond and the introduction of a second oxygen function into the cyclopentane ring

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