Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A

Joseph Sisko, James R. Henry, Steven M. Weinreb

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

An 11-step approach to tricyclic compound 42, which contains the alkaloidal nucleus of the marine natural product sarain A (1), has been developed. Pivotal steps in the construction of 42 include stereospecific intramolecular dipolar [3 + 2]-cycloaddition of an azomethine ylide generated from aziridine 27 to afford bicyclic lactam 28 and a novel intramolecular allylsilane/N-tosyliminium ion cyclication of 41 to produce the tricycle.

Original languageEnglish (US)
Pages (from-to)4945-4951
Number of pages7
JournalJournal of Organic Chemistry
Volume58
Issue number18
DOIs
StatePublished - Jan 1 1993

Fingerprint

Lactams
Cycloaddition
Biological Products
Alkaloids
Ions
allylsilane
azomethine
aziridine
sarain A

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Sisko, Joseph ; Henry, James R. ; Weinreb, Steven M. / Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A. In: Journal of Organic Chemistry. 1993 ; Vol. 58, No. 18. pp. 4945-4951.
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Development of a Strategy for Synthesis of the Unusual Marine Alkaloid Sarain A. / Sisko, Joseph; Henry, James R.; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 58, No. 18, 01.01.1993, p. 4945-4951.

Research output: Contribution to journalArticle

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