The total synthesis of (-)-suaveoline

Patrick D. Bailey, Keith M. Morgan

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

A new synthesis of the indole alkaloid (-)-suaveoline from L-tryptophan is reported (overall yield ca. 14%). Key synthetic steps include a high yielding cis-specific Pictet-Spengler reaction, a one-pot Horner-Wadsworth-Emmons and alkylation procedure, a vinylogous Thorpe cyclisation and the direct formation of a 3,4,5-trisubstituted pyridine from a 1,5-dinitrile. The direct conversion of ajmaline to semi-synthetic suaveoline is also described. © The Royal Society of Chemistry 2000.

Original languageEnglish
Pages (from-to)3578-3583
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number21
DOIs
Publication statusPublished - 2000

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