Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium-ammonia solution

Ilgiz V Galyautdinov; Zarema R Khairullina; Elvira R Zaripova; Valery P Sametov; Ekaterina S Mescheryakova; Zabir S Muslimov; Oleg S Mozgovoi; Leonard M Khalilov; Victor N Odinokov

doi:10.1016/j.steroids.2015.03.002

Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium-ammonia solution

Steroids. 2015 Jun:98:122-5. doi: 10.1016/j.steroids.2015.03.002. Epub 2015 Mar 14.

Authors

Ilgiz V Galyautdinov¹, Zarema R Khairullina², Elvira R Zaripova³, Valery P Sametov³, Ekaterina S Mescheryakova², Zabir S Muslimov², Oleg S Mozgovoi³, Leonard M Khalilov², Victor N Odinokov²

Affiliations

¹ Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation. Electronic address: ilgizphd@mail.ru.
² Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
³ Bashkir State University, Zaki Validi Street 32, 450076 Ufa, Russian Federation.

PMID: 25777947
DOI: 10.1016/j.steroids.2015.03.002

Abstract

The reaction of 20-hydroxyecdysone with methyl or ethyl iodide or allyl bromide in a lithium-ammonia solution results in stereospecific 7α-alkylation to give 7α-methyl-, 7α-ethyl-, and 7α-allyl-14-deoxy-Δ(8(14))-20-hydroxyecdysones, respectively. By catalytic hydrogenation (Pd-C/MeOH), the 7α-allyl derivative was converted to 7α-n-propyl-14-deoxy-Δ(8(14))-20-hydroxyecdysone.

Keywords: 20-Hydroxyecdysone; 7α-Alkylation; 7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ(8(14))-20-hydroxyecdysone; Lithium–ammonia solution.

MeSH terms

Alkylation
Ammonia / chemistry*
Catalysis
Ecdysterone / chemistry*
Lithium / chemistry*

Substances

Ecdysterone
Ammonia
Lithium