Daphnillonins A and B: Alkaloids Representing Two Unknown Carbon Skeletons from Daphniphyllum longeracemosum

Two highly rearranged daphniphyllum alkaloids, daphnillonins A (1) and B (2), were isolated from Daphniphyllum longeracemosum and structurally characterized by a combination of diverse methods, including the calculation of electronic circular dichroism. Compound 1 possesses an unprecedented carbon a...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3742-3747
Main Authors: Zhang, Dong-Dong, Xu, Jin-Biao, Fan, Yao-Yue, Gan, Li-She, Zhang, Hua, Yue, Jian-Min
Format: Article
Language:English
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Summary:Two highly rearranged daphniphyllum alkaloids, daphnillonins A (1) and B (2), were isolated from Daphniphyllum longeracemosum and structurally characterized by a combination of diverse methods, including the calculation of electronic circular dichroism. Compound 1 possesses an unprecedented carbon architecture with a very unique 8-methyl-6-azabicyclo[3.2.1]­octane moiety, and compound 2 represents a new carbon skeleton with an uncommon 7/6/5/7/5/5-fused ring system. The biosynthetic pathways for the two alkaloids were proposed with the concurrent major alkaloids as the precursors.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03310