This article is cited in 7 papers

Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone

N. A. Veskina, A. Sh. Ibragimova, I. V. Galyautdinov, L. M. Khalilov, V. N. Odinokov

Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation

Abstract: 9α,14α-Epoxy-14-deoxy-20-hydroxyecdysone diacetonide on treatment with NaBH₄ undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by β→α epimerization of the adjacent HC⁵ centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing β-HC⁵ configuration due to the re-epimerisation at this centre.

Keywords: ecdysteroids, oxetane cycle, 7,9-dien systeme, 25-hydroxydachryhainansterone.

Language: English

DOI: 10.1016/j.mencom.2010.09.019

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