Joong-Kwon Choi, D. Hart
1985
Citations
0
Influential Citations
76
Citations
Quality indicators
Journal
Tetrahedron
Abstract
Abstract Treatment of phenylthiolactams 5a–f with tri- n -butyltin hydride and AIBN affords mixtures of reduction and cyclization products. Cyclization products partition between indolizidinones and pyrrolizidinones depending on the terminal alkyne substituent. When the terminal substituent is a trimethylsilyl group, synthetically useful yields of pyrrolizidinones are obtained. Applications of this chemistry to the synthesis of (+)-heliotridine ( 2 ) and ( + )-hastanecine ( 3 ) via the key intermediates 37 and 38 are described.