Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 36, Pages 16292-16297Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c07198
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Funding
- National Natural Science Foundation of China [21871278, 22188101]
- Frontiers Science Center for New Organic Matter, Nankai University [63181206]
- Fundamental Research Funds for the Central Universities
- CAS Light of West China Program
- Key Program of Yunnan Province
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A bioinspired synthesis of spirochensilide A from commercially available lanosterol is reported. The synthesis involved directed C-H oxidation, Wagner-Meerwein-type double methyl migration, Meinwald rearrangement, and double-bond isomerization/spiroketal formation cascade. The proposed biosynthetic speculation was modified by this synthetic sequence, which also served as a platform for the synthesis of other lanostanes with migrating methyl groups.
A bioinspired synthesis of spirochensilide A from commercially available lanosterol is reported. The synthesis features a directed C???H oxidation, a Wagner???Meerwein-type double methyl migration, a Meinwald rearrangement, and a double-bond isomerization/spiroketal formation cascade. The proposed biosynthetic speculation was modified by this synthetic sequence, which also served as a platform for the synthesis of other lanostanes with migrating methyl groups. Superscript/Subscript Available
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