Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine

P. Wipf, C. R. Hopkins

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

The synthesis of the 1,2,3,4-tetrahydroisoquinoline moiety of tetrazomine was accomplished in 18 steps and in 3% overall yield from commercially available o-anisaldehyde. The reaction sequence utilizes a Sharpless asymmetric dihydroxylation to install the stereocenter and an intramolecular Friedel-Crafts hydroxyalkylation with an N-protected 2-oxo-acetamide to close the heterocyclic ring.

Original languageEnglish (US)
Pages (from-to)3133-3139
Number of pages7
JournalJournal of Organic Chemistry
Volume66
Issue number9
DOIs
StatePublished - May 4 2001

ASJC Scopus subject areas

  • Organic Chemistry

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