Organic Letters
Organic Letters
5 years ago

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

Synthesis and Photooxidation of the Trisubstituted Oxazole Fragment of the Marine Natural Product Salarin C
Thomas Lindel, Jan-Niklas Schäckermann
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00845

DOI: 10.1021/acs.orglett.7b00845

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