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Org Lett. 2019 Mar 1;21(5):1511-1514. doi: 10.1021/acs.orglett.9b00312. Epub 2019 Feb 15.

(±)-Xylaridines A and B, Highly Conjugated Alkaloids from the Fungus Xylaria longipes.

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1
School of Pharmaceutical Sciences , South-Central University for Nationalities , Wuhan 430074 , China.
2
College of Chemistry & Materials Science , South-Central University for Nationalities , Wuhan 430074 , China.

Abstract

Two highly conjugated alkaloids xylaridines A (1) and B (2) were obtained as racemates from the fungus Xylaria longipes. They were resoluted into optically pure enantiomers, respectively. Their structures were determined by extensive spectroscopic analyses, X-ray diffraction, and equivalent circulating density (ECD) calculations. Compound 1 possesses a 5/6/6/5/5 fused ring system with unique 2-azaspiro[4.4]nonane substructure. The hypothesis of biosynthesis pathways for 1 and 2 was proposed.

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