Delitschiapyrone A (1), an α-pyrone-naphthalenone adduct with an unprecedented pentacyclic ring system, was isolated from a solid culture of the leaf-associated fungus Delitschia sp. FL1581. The structure of 1 was elucidated by spectroscopic analysis and X-ray crystallography, and its absolute configuration was defined by experimental and calculated ECD. Biosynthetically, the unique 6/6/5/7/6 pentacyclic core of 1 may be formed by an intermolecular Diels-Alder-type addition of the precursors derived from (1′R)-2′,3′-dihydropyrenocine C (2) and 6-ethyl-2,7-dimethoxyjuglone (3) found to co-occur with 1 in this fungus.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
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Luo, J. (Creator), Wang, X. (Creator), Xu, Y. (Creator), Uren, J. M. (Contributor), Arnold, A. E. (Creator), Kong, L. (Creator), Gunatilaka, L. (Creator) & Arnold, A. E. (Creator), Cambridge Crystallographic Data Centre, 2015