Total synthesis of (±)-photodeoxytridachione through a Lewis acid catalyzed cyclization

Aubry K. Miller, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Concerted or stepwise: The concise total synthesis of the molluscan polypropionate photodeoxytridachione (3) features a Lewis acid catalyzed cyclization of tetraenoic ester 1 to form bicylo[3.1.0]hexene 2 as a key step. The stereochemistry of the cyclization can be rationalized in terms of a stepwise or a concerted mechanism.

Original languageEnglish (US)
Pages (from-to)549-552
Number of pages4
JournalAngewandte Chemie - International Edition
Volume42
Issue number5
DOIs
StatePublished - Feb 3 2003

Fingerprint

Lewis Acids
Cyclization
Stereochemistry
Acids
Esters
9,10-deoxytridachione
1-hexene

Keywords

  • Cyclization
  • Cycloaddition
  • Homogeneous catalysis
  • Lewis acids
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Total synthesis of (±)-photodeoxytridachione through a Lewis acid catalyzed cyclization. / Miller, Aubry K.; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 42, No. 5, 03.02.2003, p. 549-552.

Research output: Contribution to journalArticle

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