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A Concise Total Synthesis of (±)-Vibralactone.

ABSTRACT: 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 ?-lactone at an early stage. Cyclopropanation of the resulting bicyclic ?-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.

SUBMITTER: Nistanaki SK

PROVIDER: S-EPMC6351154 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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A Concise Total Synthesis of (±)-Vibralactone.

Nistanaki Sepand K SK Boralsky Luke A LA Pan Roy D RD Nelson Hosea M HM

Angewandte Chemie (International ed. in English) 20190109 6

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 p ...[more]

PMID: 30548983

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