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

P. Wipf, C. R. Hopkins

Research output: Contribution to journalArticle

24 Citations (Scopus)

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

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Anti-Bacterial Agents
1,2,3,4-tetrahydroisoquinoline
4-anisaldehyde
acetamide
tetrazomine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective synthesis of the AB-ring system of the antitumor antibiotic tetrazomine. / Wipf, P.; Hopkins, C. R.

In: Journal of Organic Chemistry, Vol. 66, No. 9, 04.05.2001, p. 3133-3139.

Research output: Contribution to journalArticle

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