Electron transfer initiated iminium salt photospirocyclization methodologies. Model studies for harringtonine alkaloid synthesis

T Tiner-Harding, JW Ullrich, FT Chiu…

Index: Tiner-Harding, Tammy; Ullrich, John W.; Chiu, Fang-Ting; Chen, Shyh-fong; Mariano, Patric S. Journal of Organic Chemistry, 1982 , vol. 47, # 17 p. 3360 - 3362

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Citation Number: 13

Abstract

Summary: Conjugated iminium salts, derived by O-alkylation or 0-acylation of N-allyl p- enaminones, undergo electron-transfer-initiated photocyclization reactions leading to the production of spirocyclic amines. The yields of these processes are exceptionally high when the allyl grouping of the salts possess (trimethylsily1) methyl substitution. Model studies have demonstrated the utility of these spirocyclization reactions in synthetic approaches to ...