Abstract
Compounds 1-3 isolated from Elysia diomedea are described. Compound 1 is an endoperoxide derivative of elysiapyrone A. The biomimetic-type 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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemistry
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Catalysis
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Molecular Structure
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Mollusca / chemistry
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Peroxides / chemistry*
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Pyrones / chemical synthesis*
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Pyrones / chemistry
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Reactive Oxygen Species / toxicity
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Singlet Oxygen / chemistry
Substances
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Bridged Bicyclo Compounds, Heterocyclic
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Peroxides
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Pyrones
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Reactive Oxygen Species
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elysiapyrone A
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elysiapyrone B
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Singlet Oxygen