J. Org. Chem. 85, 7, 4848-4860 (2020)
A biomimetic synthesis of chaxine and its related compounds
Niki, M., Hirata, Y., Nakazaki, A., Wu, J., Kawagishi, H., and Nishikawa, T.
The highly oxidized natural products chaxine B and BB have been synthesized from ergosterol in eight steps according to a route inspired by their proposed biosynthesis; key steps were an oxidative cascade from a furan intermediate to an enol ester using m-chloroperbenzoic acids (MCPBA), followed by diastereoselective epoxidation and acyloxy migration. This concise synthesis resulted in the revision of the structures of chaxine B and its naturally occurring analogs and syntheses of the unnatural analogues of these natural products for biological investigations.