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Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene.
Journal article

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene.

  • Tran DN Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700.
  • Cramer N
  • 2014-05-29
Published in:
  • Chemistry (Weinheim an der Bergstrasse, Germany). - 2014
bicyclogermacrene
biomimetic synthesis
cyclization
natural products
terpenes
Benzopyrans
Biological Products
Biomimetics
Crystallography, X-Ray
Cyclization
Molecular Conformation
Sesquiterpenes
Stereoisomerism
Terpenes
English (+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://folia.unifr.ch/global/documents/209822
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