4.6 Article

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

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 34, 页码 10654-10660

出版社

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

关键词

bicyclogermacrene; biomimetic synthesis; cyclization; natural products; terpenes

资金

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

向作者/读者索取更多资源

(+)-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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