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A Concise Total Synthesis of (±)-Vibralactone

preprint
revised on 24.10.2018 and posted on 24.10.2018 by Sepand Nistanaki, Luke A. Boralsky, Roy D. Pan, Hosea Nelson
Disclosed is a four-step synthesis of (±)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one forges both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone furnishes a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. Our concise and modular route to the natural product provides the shortest total synthesis of (±)-vibralactone reported to date.

Funding

T32GM008496

History

Email Address of Submitting Author

snistanaki@chem.ucla.edu

Institution

University of California, Los Angeles

Country

USA

ORCID For Submitting Author

0000-0002-5252-803X

Declaration of Conflict of Interest

No conflict of interest

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in Angewandte Chemie

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