Confirmation of the stereochemistry of spiroviolene

Yao Kong; Yuanning Liu; Kaibiao Wang; Tao Wang; Chen Wang; Ben Ai; Hongli Jia; Guohui Pan; Min Yin; Zhengren Xu

doi:10.3762/bjoc.20.77

Beilstein Journal of Organic Chemistry (Apr 2024)

Confirmation of the stereochemistry of spiroviolene

Yao Kong,
Yuanning Liu,
Kaibiao Wang,
Tao Wang,
Chen Wang,
Ben Ai,
Hongli Jia,
Guohui Pan,
Min Yin,
Zhengren Xu

Affiliations

Yao Kong: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Yuanning Liu: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Kaibiao Wang: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Tao Wang: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Chen Wang: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Ben Ai: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Hongli Jia: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China
Guohui Pan: State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China; University of Chinese Academy of Sciences, Beijing 100049, China
Min Yin: School of Medicine, Yunnan University, 2 North Cui Hu Road, Kunming 650091, China
Zhengren Xu: State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China; Ningbo Institute of Marine Medicine, Peking University, Ningbo 315010, China

DOI: https://doi.org/10.3762/bjoc.20.77
Journal volume & issue: Vol. 20, no. 1
pp. 852 – 858

Abstract

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We confirm the previously revised stereochemistry of spiroviolene by X-ray crystallographically characterizing a hydrazone derivative of 9-oxospiroviolane, which is synthesized by hydroboration/oxidation of spiroviolene followed by oxidation of the resultant hydroxy group. An unexpected thermal boron migration occurred during the hydroboration process of spiroviolene that resulted in the production of a mixture of 1α-hydroxyspiroviolane, 9α- and 9β-hydroxyspiroviolane after oxidation. The assertion of the cis-orientation of the 19- and 20-methyl groups provided further support for the revised cyclization mechanism of spiroviolene.

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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