An Approach to Total Synthesis of (+)-Lycoricidine

Matthias C. McIntosh, Steven M. Weinreb

Research output: Contribution to journalArticle

99 Scopus citations

Abstract

A convergent synthesis of a protected version of (+)-lycoricidine has been accomplished in 13 steps from l-arabinose. Preparation of the aminocyclitol moiety 50 employed a novel vinylsilane-terminated N-sulfonyliminium ion cyclization of vinylsilane aldehyde 42. Closure of the B-ring using an intramolecular Heck reaction afforded lycoricidine derivative 58. An unexpected cyclization of vinylsilane aldehyde 42 allowed for the stereodivergent preparation of semiprotected conduritols 43 and 45.

Original languageEnglish (US)
Pages (from-to)4823-4832
Number of pages10
JournalJournal of Organic Chemistry
Volume58
Issue number18
DOIs
StatePublished - Jan 1 1993

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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