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Paper | Regular issue | Vol 31, No. 2, 1990, pp.283-287
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5224
Synthesis of (±)-Physovenine and (±)-7-Bromophysovenine from Intermediates of the Synthesis of Physostigmines

Yi-lin Luo, Qian-sheng Yu, Linda Chrisey, and Arnold Brossi*

*Section of Medical Chemistry, Laboratory of Analytical Chemistry, NIDDK, National Institute of Health, Bethesda, MD 20982, U.S.A.

Abstract

Facile synthesis of (±)-physovenine (1) was accomplised from oxindole 3, an intermediate in Julian’s total synthesis of physostigmines (2A and 2B). C-Alkylation of 3 with methyl bromoacetate afforded ester 4 which was reduced with LAH in THF at 0 °C to directrly afford tetrahydrofuroindole 6. Ether cleavage of 6 with BBr3 in dichloromethane afforded phenol 7, and (±)-physovenine (1) on treatment of 7 with methyl isocyanate in ehter. Bromination of 1 with bromosuccinimide in methanol afforded (±)-7-bromophysovenine (8).