Total synthesis of marine natural products separacenes A and B

Org Biomol Chem. 2017 Jun 7;15(22):4842-4850. doi: 10.1039/c7ob00345e.

Abstract

A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C7-C9 conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C5-C6 and C11-C12 olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Molecular Structure
  • Polyenes / chemical synthesis*
  • Polyenes / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Polyenes
  • separacene A
  • separacene B