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Beilstein Journal of Organic Chemistry
Article . 2024 . Peer-reviewed
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https://doi.org/10.3762/bxiv.2...
Article . 2023 . Peer-reviewed
License: CC BY
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Confirmation of the stereochemistry of spiroviolene

Authors: Yao Kong; Yuanning Liu; Kaibiao Wang; Tao Wang; Chen Wang; Ben Ai; Hongli Jia; +3 Authors

Confirmation of the stereochemistry of spiroviolene

Abstract

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.

Related Organizations
Keywords

QD241-441, Letter, Science, Q, stereochemistry, spiroviolene, Organic chemistry, boron migration, diterpene

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
1
Average
Average
Average
Green
Published in a Diamond OA journal