7α-alkylation and 7,7-bis-alkylation of 20-hydroxyecdysone with propargyl bromide in a lithium-ammonia solution and catalytic reductive spirocyclization of 7,7-bis(2-propyn-1-yl)-14-deoxy-Δ(8(14))-20-hydroxyecdysone

7α-Alkylation and 7,7-bis-alkylation of 20-hydroxyecdysone with propargyl bromide in a lithium-ammonia solution resulted in the formation of 7α-(2-propyn-1-yl)- and 7,7-bis(2-propyn-1-yl)-14-deoxy-Δ(8(14))-20-hydroxyecdysone in 92% and 75% yield respectively. Upon catalytic hydrogenation (10% Pd-C)...

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Veröffentlicht in:Steroids 2016-03, Vol.107, p.121-127
Hauptverfasser: Galyautdinov, Ilgiz V, Khairullina, Zarema R, Sametov, Valery P, Muslimov, Zabir S, Khalilov, Leonard M, Odinokov, Victor N
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Sprache:eng
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Zusammenfassung:7α-Alkylation and 7,7-bis-alkylation of 20-hydroxyecdysone with propargyl bromide in a lithium-ammonia solution resulted in the formation of 7α-(2-propyn-1-yl)- and 7,7-bis(2-propyn-1-yl)-14-deoxy-Δ(8(14))-20-hydroxyecdysone in 92% and 75% yield respectively. Upon catalytic hydrogenation (10% Pd-C) of 7,7-bis(2-propyn-1-yl) derivative spirocyclization occurs by geminal 2-propyn-1-yl groups.
ISSN:1878-5867
DOI:10.1016/j.steroids.2016.01.002