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Bioinspired Synthesis of Spirochensilide A from Lanosterol
- Source :
- Journal of the American Chemical Society. 144(36)
- Publication Year :
- 2022
-
Abstract
- 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.
Details
- ISSN :
- 15205126
- Volume :
- 144
- Issue :
- 36
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....3fcfaf21c76083b5855b88f2c1de0deb