Total Synthesis of (±)-Epiisocomenes VIA Hydrogenation of “Chatterjee's Ketone”

Abstract

Dienic acid 5 was transformed into tricyclic ketone 6 in four steps using the cyclopentene annulation of dienic diazoketones. Hydrogenation of 6 under several conditions yielded ketone 7a which was further transformed into β-epiisocomene 4 and epiisocomene 3, contrary to the results previously reported by Samir Chatterjee.