A Concise Total Synthesis of (±)‐Vibralactone. Issue 6 (9th January 2019)

• Record Type: Journal Article
• Authors: Nistanaki, Sepand K.; Boralsky, Luke A.; Pan, Roy D.; Nelson, Hosea M.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 6(2019)
• Page Start: 1724
• Page End: 1726
• Publication Date: 2019-01-09
• Subjects: cyclopropanation -- housane -- photochemistry -- ring expansion -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201812711
• Languages: English
• ISSNs: 1433-7851

Abstract

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 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. Abstract : Bringing the housane down : The five‐step synthesis of (±)‐vibralactone, a biologically active terpenoid natural product, is described. This is the shortest total synthesis of (±)‐vibralactone reported to date.