Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes

Matthew D Norris; Michael V Perkins

doi:10.1021/acs.joc.6b01196

Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes

J Org Chem. 2016 Aug 5;81(15):6848-54. doi: 10.1021/acs.joc.6b01196. Epub 2016 Jul 21.

Authors

Matthew D Norris¹, Michael V Perkins¹

Affiliation

¹ School of Chemical and Physical Sciences, Flinders University , GPO Box 2100, Adelaide, SA 5001, Australia.

PMID: 27359169
DOI: 10.1021/acs.joc.6b01196

Abstract

A chemoselective oxidative cleavage of synthetic gracilioether B, 11-epi-gracilioether C benzoate, and des-hydroxygracilioether C with pyridinium chlorochromate, which proceeds with loss of the furanyl acetate, has enabled total synthesis and stereochemical elucidation of the marine sponge metabolites (4R,6R)-plakilactone C, (4R,6R,9R)-plakilactone B, and (4R,6R)-des-hydroxyplakilactone B. des-Hydroxygracilioether C, the putative biosynthetic precursor to hippolachnin A, was also found to undergo a facile ene cyclization on treatment with SnCl4.

Publication types

Research Support, Non-U.S. Gov't