Synthetic Transformation of Abietic Acid IIIa. Photoconversion of Diene Adducts

Abstract

Diels-Alder addition of 2-chloroacrylonitrile to the abietic acid skeleton affords, via an -chloronitrile adduct, the tetracyclic ,-unsaturated ketone 1. Photochemical conversions of 1 to 2 and 3 are described. The cyclopropane ring of 3 is cleaved by a Birch reduction yielding 4.

Diterpenoids (1998)

“…78 The Friedel-Crafts acylation and deisopropylation of methyl dehydroabietate has been described. 79 A number of investigations have been reported [80][81][82] into the chemistry of the Diels-Alder adducts of abietic acid and into the oxidation of rings B and C. 83 5 Tetracyclic diterpenoids…”