Canadian journal of chemistry

C19 quassinoid model studies: Preparation of trans-perhydroindans via a vinylogous Mukaiyama aldol free-radical cyclization route

MG Donahue, DJ Hart

Index: Donahue, Matthew G.; Hart, David J. Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 314 - 317

Full Text: HTML

Citation Number: 8

Abstract

Aldehyde 9 was prepared in 5 steps from 3, 5-dimethylbenzoic acid. Treatment of 9 with ketene acetals 10 and 19 and titanium tetrachloride gave free-radical cyclization substrates 11 and 20 in 67% and 51% yields, respectively. Tri-n-butylstannane-mediated cyclization of 11 and 20 gave trans-perhydroindans 14 and 21 in 60% and 63% yields, respectively. The relationship of these studies to an approach to C19 quassinoids is discussed. Key words: ...