Development of novel Lewis acid catalyzed cycloisomerizations: Synthesis of bicyclo[3.1.0]hexenes and cyclopentenones

Aubry K. Miller, Matthew R. Banghart, Christopher M. Beaudry, Judy M. Suh, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The Lewis acid catalyzed cyclization of hexatrienes and pentadienals to bicyclo[3.1.0]hexenes and cyclopentenones, respectively, was investigated. The application of the former reaction to the total synthesis of photodeoxytridachione, a molluscan polypropionate, is described.

Original languageEnglish (US)
Pages (from-to)8919-8930
Number of pages12
JournalTetrahedron
Volume59
Issue number45
DOIs
StatePublished - Nov 3 2003

Fingerprint

Lewis Acids
Cyclization
cyclopentenone
1-hexene
9,10-deoxytridachione

Keywords

  • Cycloisomerization
  • Lewis acid
  • Molluscan polypropionate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Development of novel Lewis acid catalyzed cycloisomerizations : Synthesis of bicyclo[3.1.0]hexenes and cyclopentenones. / Miller, Aubry K.; Banghart, Matthew R.; Beaudry, Christopher M.; Suh, Judy M.; Trauner, Dirk.

In: Tetrahedron, Vol. 59, No. 45, 03.11.2003, p. 8919-8930.

Research output: Contribution to journalArticle

Miller, Aubry K. ; Banghart, Matthew R. ; Beaudry, Christopher M. ; Suh, Judy M. ; Trauner, Dirk. / Development of novel Lewis acid catalyzed cycloisomerizations : Synthesis of bicyclo[3.1.0]hexenes and cyclopentenones. In: Tetrahedron. 2003 ; Vol. 59, No. 45. pp. 8919-8930.
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