4.6 Article

Biomimetic Synthesis of (+)-Ledene, (+)-Viridiflorol, (-)-Palustrol, (+)-Spathulenol, and Psiguadial A, C, and D via the Platform Terpene (+)-Bicyclogermacrene

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 34, Pages 10654-10660

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403082

Keywords

bicyclogermacrene; biomimetic synthesis; cyclization; natural products; terpenes

Funding

  1. Swiss National Science Foundation [137666]
  2. EPFL

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(+)-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.

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