Hydroxylation and epimerization of ecdysteroids in alkaline media: stereoselective synthesis of 9α-hydroxy-5α-ecdysteroids

Rimma G Savchenko; Svetlana A Kostyleva; Vadim V Kachala; Leonard M Khalilov; Victor N Odinokov

doi:10.1016/j.steroids.2014.06.019

Hydroxylation and epimerization of ecdysteroids in alkaline media: stereoselective synthesis of 9α-hydroxy-5α-ecdysteroids

Steroids. 2014 Oct:88:101-5. doi: 10.1016/j.steroids.2014.06.019. Epub 2014 Jul 3.

Authors

Rimma G Savchenko¹, Svetlana A Kostyleva², Vadim V Kachala³, Leonard M Khalilov², Victor N Odinokov²

Affiliations

¹ Institute of Petrochemistry and Catalysis, Russian Academy of Science, Laboratory of Organic Synthesis, Prospekt Oktyabrya 141, 450075 Ufa, Russian Federation. Electronic address: rimasavchenko@mail.ru.
² Institute of Petrochemistry and Catalysis, Russian Academy of Science, Laboratory of Organic Synthesis, Prospekt Oktyabrya 141, 450075 Ufa, Russian Federation.
³ N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119991 Moscow, Russian Federation.

PMID: 24998869
DOI: 10.1016/j.steroids.2014.06.019

Abstract

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.

Keywords: Autoxidation; Ecdysteroids; Epimerization; Hydrogenation.

MeSH terms

Chemistry Techniques, Synthetic
Ecdysteroids / chemical synthesis*
Ecdysteroids / chemistry*
Hydrogen-Ion Concentration
Hydroxylation
Methanol / chemistry
Sodium Hydroxide / chemistry
Stereoisomerism
Substrate Specificity

Substances

Ecdysteroids
Sodium Hydroxide
Methanol