A Concise Total Synthesis of (±)-Vibralactone.

Autor: Nistanaki SK; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA., Boralsky LA; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA., Pan RD; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA., Nelson HM; Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Feb 04; Vol. 58 (6), pp. 1724-1726. Date of Electronic Publication: 2019 Jan 09.
DOI: 10.1002/anie.201812711
Abstrakt: Disclosed is a five-step synthesis of (±)-vibralactone, a biologically active terpenoid natural product. A key photochemical valence isomerization of 3-prenyl-pyran-2-one produces both the all-carbon quaternary stereocenter and the β-lactone at an early stage. Cyclopropanation of the resulting bicyclic β-lactone produces a strained housane structure that is converted to the natural product through a sequential ring expansion and reduction strategy. This concise and modular route to the natural product provides the shortest total synthesis of (±)-vibralactone reported to date.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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