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Communication | Regular issue | Vol 36, No. 6, 1993, pp.1199-1204
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6313
Asymmetric Synthesis of α-Substituted 5-Hydroxytryptophan Derivatives

David Crich* and Linda B. L. Lim

*Department of Chemistry (M/C 111), University of Illinois at Chicago, 801 West Taylor St. , Chicago, IL 60607-7061, U.S.A.

Abstract

5-Hydroxytryptophan was converted to pyrroloindole (3), which on deprotonation with LDA and subsequent reaction with alkyl halides gave the C-2 alkylated derivatives (6-9) cleanly with retention of configuration. Reversion to the 5-hydroxytryptophan skeleton was then achieved by stirring in trifluoroacetic acid and deprotection by treatment with sodium in liquid ammonia followed by saponification.