Enantiospecific Synthesis of (-)-Tabtoxinine β-Lactam

Roland E. Dolle, Chun Sing Li, Riccardo Novelli, Lawrence I. Kruse, Drake Eggleston

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

A convergent, 10-step synthesis of optically active tabtoxinine β-lactam [(-)-1] has been described. Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 → 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a. Synthons (-)-4 and 3 are available on a semipreparative scale.

Original languageEnglish
Pages (from-to)128-132
Number of pages5
JournalJournal of Organic Chemistry
Volume57
Issue number1
DOIs
StatePublished - Jan 1 1992
Externally publishedYes

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