Synthesis of 3- epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow

Org Lett. 2022 Jun 24;24(24):4305-4309. doi: 10.1021/acs.orglett.2c00689. Epub 2022 May 10.

Abstract

A synthesis of 3-epi-hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, is reported. The carbon skeleton was prepared by functionalization of a cyclopentanone and an intramolecular Mukaiyama aldol reaction. Highlights include a late-stage photo-oxidation of a methoxyallene to provide an ester group. The problems encountered in the batch process were solved by translation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging late-stage transformations in natural product synthesis.

MeSH terms

  • Biological Products* / chemistry
  • Esters
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Biological Products
  • Esters