Structural Reassignment of Cytosporolides A–C via Biomimetic Synthetic Studies and Reinterpretation of NMR Data

A structure revision for the recently isolated fungal meroterpenoids, cytosporolides A–C, is suggested based on biosynthetic speculation and reinterpretation of existing spectroscopic data. The structure revision is supported by a biomimetic synthetic study, featuring a [4 + 2] cycloaddition reactio...

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Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (19), p.5318-5321
Main Authors: Spence, Justin T. J, George, Jonathan H
Format: Article
Language:English
Subjects:
Biomimetic Materials - chemical synthesis
Cyclization
Magnetic Resonance Spectroscopy
Molecular Structure
Sesquiterpenes - chemical synthesis
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Summary:A structure revision for the recently isolated fungal meroterpenoids, cytosporolides A–C, is suggested based on biosynthetic speculation and reinterpretation of existing spectroscopic data. The structure revision is supported by a biomimetic synthetic study, featuring a [4 + 2] cycloaddition reaction between a presumed o-quinone methide intermediate and β-caryophyllene.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202181g