Bioinspired Synthesis of Spirochensilide A from Lanosterol.

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.

Citation

Xianwen Long, Jun Li, Feng Gao, Hai Wu, Jun Deng. Bioinspired Synthesis of Spirochensilide A from Lanosterol. Journal of the American Chemical Society. 2022 Sep 14;144(36):16292-16297

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PMID: 36054904

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