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Synthesis of a caryophyllene isoprenologue, a potential diterpene natural product

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
61
Issue
15
Identifiers
DOI: 10.1016/j.tet.2005.02.018
Keywords
  • Bicyclic Diterpene
  • Flexibilene
  • Wittig Reaction
  • Warren Modification
  • Mcmurry Cyclization

Abstract

Abstract (−)-β-Caryophyllene has been converted into three stereoisomers of a new bicyclic compound that is structurally related to the known macrocyclic diterpene, flexibilene, in the same way β-caryophyllene is related to humulene. Key steps are selective cleavage of caryophyllene, addition of a five carbon component by a Wittig reaction and McMurry cyclization.

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