Synthesis of 2,5- and 2,6-norbornane derivatives with prostaglandin-like side chains

Abstract

Norborn-5-en-2-endo-ylmethyl toluene-4-sulphonate, readily prepared from the Diels–Alder adduct of cyclopentadiene and acrylic acid, has been converted, in six and seven stages respectively, into the prostaglandin-like compounds 2-endo-(6-carboxyhex-2-enyl)norbornan-5- and -6-exo-yl 2-hydr-oxyheptyl ethers. The synthesis of the former compounds involves a novel hydroxyethoxy mercuriation of a norbornene double bond.