Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 34, Pages 10654-10660Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403082
Keywords
bicyclogermacrene; biomimetic synthesis; cyclization; natural products; terpenes
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Funding
- Swiss National Science Foundation [137666]
- 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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