Validating an endoperoxide as a key intermediate in the biosynthesis of elysiapyrones

Abstract

Compounds 1-3 isolated from Elysia diomedea are described. Compound 1 is an endoperoxide derivative of elysiapyrone A. The biomimetictype transformation of compound 1 to elysiapyrone A catalyzed by neutral base transformed the endoperoxide to a vicinal diepoxide, thus suggesting the endoperoxide as a key intermediate in the biosynthesis of elysiapyrone A. A biogenetic pathway for their formation involving a cycloaddition of singlet oxygen to a polypropionate alkenyl open chain is proposed.

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Diaz-Marrero, Ana R., Cueto, Mercedes, D'Croz, Luis, and Darias, Jose. 2008. "<a href="https://repository.si.edu/handle/10088/11855">Validating an endoperoxide as a key intermediate in the biosynthesis of elysiapyrones</a>." <em>Organic letters</em>, 10, (14) 3057–3060. <a href="https://doi.org/10.1021/ol8010425">https://doi.org/10.1021/ol8010425</a>.

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