Total Synthesis of the Resorcyclic Acid Lactone Spiroketal Citreoviranol

J Org Chem. 2016 Sep 16;81(18):8343-50. doi: 10.1021/acs.joc.6b01503. Epub 2016 Aug 29.

Abstract

The first total synthesis of resorcyclic acid lactone spiroketal citreoviranol (1) is described. The synthesis was completed in nine steps and via Sonogashira cross-coupling, gold-catalyzed cyclization, and an unusual base-induced ketalization. The relative and absolute stereochemistry of citreoviranol was unambiguously confirmed using 2D NMR spectroscopy and X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't