doi: 10.1021/acs.orglett.7b00845.
Epub 2017 Apr 20.
Synthesis and Photooxidation of the Trisubstituted Oxazole Fragment of the Marine Natural Product Salarin C
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- PMID: 28425712
- DOI: 10.1021/acs.orglett.7b00845
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Synthesis and Photooxidation of the Trisubstituted Oxazole Fragment of the Marine Natural Product Salarin C
Org Lett.
.
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.
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