Xylaridines C and D, Unusual Thiopyranodipyridine Alkaloids from the Fungus Xylaria longipes

Structurally unique thiopyranodipyridine alkaloids xylaridines C (1) and D (2) were isolated from the fungus Xylaria longipes. Their structures were established by comprehensive spectroscopic analysis combined with single-crystal X-ray diffraction and electron-capture detection (ECD) calculations. C...

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Bibliographic Details
Published in:Organic letters 2019-08, Vol.21 (15), p.6145-6148
Main Authors: Li, Jing, Wang, Wen-Xuan, Li, Zheng-Hui, He, Juan, Huang, Rong, Zheng, Yong-Sheng, Li, Lan-Qing, Wang, Xian, Feng, Tao, Liu, Ji-Kai
Format: Article
Language:English
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Summary:Structurally unique thiopyranodipyridine alkaloids xylaridines C (1) and D (2) were isolated from the fungus Xylaria longipes. Their structures were established by comprehensive spectroscopic analysis combined with single-crystal X-ray diffraction and electron-capture detection (ECD) calculations. Compound 1 possesses two piperidine moieties fused with a centered thiopyran ring, while compound 2 is a dimer of 1. Compound 1 was resoluted into optical pure enatiomers (+)-1 and (−)-1 by chiral HPLC. Moreover, compound 2 was resoluted into an optically pure compound (+)-2 and a mixture of (−)-2 and meso-2. Plausible biosynthetic pathways of compounds 1 and 2 are proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02311