Synthesis and Photooxidation of the Trisubstituted Oxazole Fragment of the Marine Natural Product Salarin C

Org Lett. 2017 May 5;19(9):2306-2309. doi: 10.1021/acs.orglett.7b00845. Epub 2017 Apr 20.

Abstract

The eastern section of the macrocyclic marine natural product salarin C from the sponge Fascaplysinopsis sp. was synthesized employing a halogen dance reaction to assemble the trisubstituted oxazole moiety. The synthesis was inspired by Kashman's hypothesis on the biomimetic oxidation of salarin C to salarin A. Clean conversion to the triacylamine partial structure of salarin A occurred on treatment with photochemically generated singlet oxygen. Thus, a Wasserman-type oxidative rearrangement is chemically possible in this case.

Publication types

  • Research Support, Non-U.S. Gov't