A Concise Total Synthesis of (±)‐Vibralactone

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.

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.

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