Synthesis and use of 7-substituted norbornadienes for the preparation of prostaglandins and prostanoids

Abstract

Syntheses of 7-substituted norbornadienes from 7-t-butoxy- and 7-halogeno-norbornadienes are described. Rearrangement of the products in the presence of peracetic acid gives bicyclic aldehydes (2) in equilibrium with enol ethers (3) which are hydrolysed to hydroxycyclopentenylacetaldehydes (4), and converted into key intermediates for the synthesis of prostaglandins and their analogues. Syntheses of prostaglandin J analogues with n-hexyl and phenyl groups replacing the ω-side-chain are described.