The Journal of Organic Chemistry

Stereocontrolled total synthesis of. alpha.-and. beta.-santonin

JA Marshall, PGM Wuts

Index: Marshall,J.A.; Wuts,P.G.M. Journal of Organic Chemistry, 1978 , vol. 43, # 6 p. 1086 - 1089

Full Text: HTML

Citation Number: 28

Abstract

A ttstal synthesis of racemic cy-and p-santonin is described. The synthetic sequence invo) ves reduction-alkylation of m-toluic acid with lithium in ammonia followed by methyl iodide. Homologation of the resulting l-methyl-1, 4-dihydro-m-toluic acid was effected by reduction using lithium aluminum hydride, oxidation with N-chlorosuccinimide-dimethyl sulfide reagent, and condensation of the resulting aldehyde with triethyl phosphonoacetate to ...