A Kinetic Dearomatization Strategy for an Expedient Biomimetic Route to the Bielschowskysin Skeleton

Paul Scesa, Medhi Wangpaichitr, Niramol Savaraj, Lyndon West, Stéphane P. Roche

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Bielschowskysin (1), the flagship of the furanocembranoid diterpene family, has attracted attention from chemists owing to its intriguing and daunting polycyclic architecture and medicinal potential against lung cancer. The high level of functionalization of 1 poses a considerable challenge to synthesis. Herein, a stereoselective furan dearomatization strategy of furanocembranoids was achieved via the intermediacy of chlorohydrins. The stereochemical course of the kinetic dearomatization was established, and the C3 configuration of the resulting exo-enol ether intermediates proved to be essential to complete the late-stage transannular [2+2] photocycloaddition. Overall, this biomimetic strategy starting from the natural product acerosolide (9) featured an unprecedented regio- and highly stereoselective furan dearomatization, which provided rapid access to the pivotal exo-enol ethers en route to the intricate bielschowskyane skeleton.

Original languageEnglish (US)
Pages (from-to)1316-1321
Number of pages6
JournalAngewandte Chemie - International Edition
Volume57
Issue number5
DOIs
StatePublished - Jan 26 2018

Keywords

  • bielschowskysin
  • biomimetic synthesis
  • furanocembranoids
  • kinetic dearomatization
  • natural products

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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