Article ID Journal Published Year Pages File Type
2027892 Steroids 2014 5 Pages PDF
Abstract

•In NaOH–MeOH ecdysteroids undergo epimerization and autoxydation.•The new 9α-hydroxy-5α-ecdysteroids are synthesized in alkaline media.•5α-Epimer of the natural ecdysteroid 9α-hydroxyecdysterone is synthesized.•The hydrogenation of 9α-hydroxy-5α-ecdysteroids leads to the 7,8 α-dihydroderivatives.

Autoxidation of diacetonides of 20-hydroxyecdysone and ponasterone A under treatment with excess of NaOH in methanol leads to the formation of 9α-hydroxy-5α-ecdysteroids previously not described. Their structures have been determined by detailed NMR analysis. Catalytic hydrogenation (Pd-C, MeOH–MeONa) of hydroxylated ecdysteroids affords the 7,8α-dihydro-9α-hydroxy-5α-ecdysteroids.

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