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

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 circulat...

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Published inOrganic letters Vol. 21; no. 5; pp. 1511 - 1514
Main Authors Li, Jing, Wang, Wen-Xuan, Chen, He-Ping, Li, Zheng-Hui, He, Juan, Zheng, Yong-Sheng, Sun, Huan, Huang, Rong, Yuan, Qing-Xia, Wang, Xian, Feng, Tao, Liu, Ji-Kai
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.03.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY METABOLITES
SESQUITERPENES
REDUCTION
CONSTITUENTS
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Summary: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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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00312