Delitschiapyrone A, a pyrone-naphthalenone adduct bearing a new pentacyclic ring system from the leaf-associated fungus Delitschia sp. FL1581

Jian Guang Luo, Xiao Bing Wang, Ya Ming Xu, Jana M. Uren, A. Elizabeth Arnold, Ling Yi Kong, A. A.Leslie Gunatilaka

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)5944-5947
Number of pages4
JournalOrganic Letters
Volume16
Issue number22
DOIs
StatePublished - Nov 21 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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