The enantioselective synthesis of (-)-Physostigmine via chiral sulfoxides

JP Marino, S Bogdan, K Kimura

Index: Marino; Bogdan; Kimura Journal of the American Chemical Society, 1992 , vol. 114, # 14 p. 5566 - 5572

Full Text: HTML

Citation Number: 107

Abstract

Abstract: The total synthesis of naturally occurring (-)-physostigmine is described. The key element for the asymmetric induction is the chirality transfer from optically active 2- (alkylsulfinyl) indoles to indoline butyrolactones bearing two chiral centers. Novel features of this synthesis involve the use of a new class of sulfoxylating agents, N-(alkylsulfinyl) oxazolidinones, to prepare the starting indolyl sulfoxides and the correlation of the size of ...