Delitschiapyrone A, a Pyrone–Naphthalenone Adduct Bearing a New Pentacyclic Ring System from the Leaf-Associated Fungus Delitschia sp. FL1581 | Zendy

Jian-Guang Luo | Zendy; Xiaobing Wang | Zendy; Ya-ming Xu | Zendy; Jana M. U′Ren | Zendy; A. Elizabeth Arnold | Zendy; Ling-Yi Kong | Zendy; A. A. Leslie Gunatilaka | Zendy

Open Access

Delitschiapyrone A, a Pyrone–Naphthalenone Adduct Bearing a New Pentacyclic Ring System from the Leaf-Associated Fungus Delitschia sp. FL1581

Author(s) -

Jian-Guang Luo,

Xiaobing Wang,

Ya-ming Xu,

Jana M. U′Ren,

A. Elizabeth Arnold,

Ling-Yi Kong,

A. A. Leslie Gunatilaka

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502973c

Subject(s) - chemistry , pyrone , adduct , ring (chemistry) , fungus , bearing (navigation) , stereochemistry , organic chemistry , botany , biology , cartography , geography

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.

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