Confirmation of the Stereochemistry of Spiroviolene

Submitting author affiliation:
Peking University, Beijing, China

Beilstein Arch. 2023, 202368. https://doi.org/10.3762/bxiv.2023.68.v1

Published 28 Dec 2023

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Abstract

We confirm the previously revised stereochemistry of spiroviolene by X-ray crystallographically characterizing a hydrazone derivative of 9-oxo-spiroviolane, which is synthesized from 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 have resulted in the production of a mixture of 1α-hydroxy-spiroviolane, 9α- and 9β-hydroxy-spiroviolane after oxidation. The assertion of the cis-oriented 19- and 20-methyl groups has provided further support for the revised cyclization mechanism of spiroviolene.

Keywords: diterpene; stereochemistry; spiroviolene; boron migration

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Kong, Y.; Liu, Y.; Wang, K.; Wang, T.; Wang, C.; Ai, B.; Jia, H.; Pan, G.; Yin, M.; Xu, Z. Beilstein Arch. 2023, 202368. doi:10.3762/bxiv.2023.68.v1

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