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Victor N Odinokov - One of the best experts on this subject based on the ideXlab platform.
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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 δ8 14 20 hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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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-Δ8(14)-20-Hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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Stereospecific 7α-alkylation of 20-Hydroxyecdysone in a lithium-ammonia solution.
Steroids, 2015Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Elvira R. Zaripova, Ekaterina S. Mescheryakova, Oleg S. Mozgovoi, Victor N OdinokovAbstract: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.
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20-Hydroxyecdysone oximes and their rearrangement into lactams
Russian Journal of Organic Chemistry, 2009Co-Authors: R. V. Shafikov, Leonard M. Khalilov, Ya. R. Urazaeva, S. R. Afon’kina, Rimma G. Savchenko, Victor N OdinokovAbstract:(E)-Oximes derived from 20-Hydroxyecdysone diacetonides and 7,8-dihydro analog were converted into the corresponding lactams (6-oxo-5a-aza-5a-homo derivatives) via Beckmann rearrangement. 14,15-Anhydro-20-Hydroxyecdysone (Z)-oxime under analogous conditions (reaction with p-toluenesulfonyl chloride in acetone in the presence of Na2CO3) gave rise to 20-hydroxyecdisone 20,22-acetonide (Z)-O-tosyloxime which did not undergo Beckmann rearrangement.
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Unexpected formation of an oxetane cycle by oxidation of diacetonide of 20-Hydroxyecdysone with oxygen in an alkaline medium
Mendeleev Communications, 2008Co-Authors: Victor N Odinokov, I V Galyautdinov, Leonard M. Khalilov, Aliya Sh. Ibragimova, N. A. Ves’kina, Fedor M. Dolgushin, Zoya A. StarikovaAbstract:The diacetonides of 9α,14α-epoxy-14-deoxy-20-Hydroxyecdysone and 14α-hydroperoxy-14-deoxy-20-Hydroxyecdysone have been obtained by the interaction of diacetonide of 20-Hydroxyecdysone with a solution of lithium in liquid ammonia and following treatment with ammonia chloride and atmospheric oxygen.
I V Galyautdinov - One of the best experts on this subject based on the ideXlab platform.
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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 δ8 14 20 hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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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-Δ8(14)-20-Hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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Stereospecific 7α-alkylation of 20-Hydroxyecdysone in a lithium-ammonia solution.
Steroids, 2015Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Elvira R. Zaripova, Ekaterina S. Mescheryakova, Oleg S. Mozgovoi, Victor N OdinokovAbstract: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.
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Unexpected formation of an oxetane cycle by oxidation of diacetonide of 20-Hydroxyecdysone with oxygen in an alkaline medium
Mendeleev Communications, 2008Co-Authors: Victor N Odinokov, I V Galyautdinov, Leonard M. Khalilov, Aliya Sh. Ibragimova, N. A. Ves’kina, Fedor M. Dolgushin, Zoya A. StarikovaAbstract:The diacetonides of 9α,14α-epoxy-14-deoxy-20-Hydroxyecdysone and 14α-hydroperoxy-14-deoxy-20-Hydroxyecdysone have been obtained by the interaction of diacetonide of 20-Hydroxyecdysone with a solution of lithium in liquid ammonia and following treatment with ammonia chloride and atmospheric oxygen.
Leonard M. Khalilov - One of the best experts on this subject based on the ideXlab platform.
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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 δ8 14 20 hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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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-Δ8(14)-20-Hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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Stereospecific 7α-alkylation of 20-Hydroxyecdysone in a lithium-ammonia solution.
Steroids, 2015Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Elvira R. Zaripova, Ekaterina S. Mescheryakova, Oleg S. Mozgovoi, Victor N OdinokovAbstract: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.
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20-Hydroxyecdysone oximes and their rearrangement into lactams
Russian Journal of Organic Chemistry, 2009Co-Authors: R. V. Shafikov, Leonard M. Khalilov, Ya. R. Urazaeva, S. R. Afon’kina, Rimma G. Savchenko, Victor N OdinokovAbstract:(E)-Oximes derived from 20-Hydroxyecdysone diacetonides and 7,8-dihydro analog were converted into the corresponding lactams (6-oxo-5a-aza-5a-homo derivatives) via Beckmann rearrangement. 14,15-Anhydro-20-Hydroxyecdysone (Z)-oxime under analogous conditions (reaction with p-toluenesulfonyl chloride in acetone in the presence of Na2CO3) gave rise to 20-hydroxyecdisone 20,22-acetonide (Z)-O-tosyloxime which did not undergo Beckmann rearrangement.
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Unexpected formation of an oxetane cycle by oxidation of diacetonide of 20-Hydroxyecdysone with oxygen in an alkaline medium
Mendeleev Communications, 2008Co-Authors: Victor N Odinokov, I V Galyautdinov, Leonard M. Khalilov, Aliya Sh. Ibragimova, N. A. Ves’kina, Fedor M. Dolgushin, Zoya A. StarikovaAbstract:The diacetonides of 9α,14α-epoxy-14-deoxy-20-Hydroxyecdysone and 14α-hydroperoxy-14-deoxy-20-Hydroxyecdysone have been obtained by the interaction of diacetonide of 20-Hydroxyecdysone with a solution of lithium in liquid ammonia and following treatment with ammonia chloride and atmospheric oxygen.
Zarema R Khairullina - One of the best experts on this subject based on the ideXlab platform.
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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 δ8 14 20 hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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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-Δ8(14)-20-Hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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Stereospecific 7α-alkylation of 20-Hydroxyecdysone in a lithium-ammonia solution.
Steroids, 2015Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Elvira R. Zaripova, Ekaterina S. Mescheryakova, Oleg S. Mozgovoi, Victor N OdinokovAbstract: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.
Valery P Sametov - One of the best experts on this subject based on the ideXlab platform.
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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 δ8 14 20 hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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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-Δ8(14)-20-Hydroxyecdysone
Steroids, 2016Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Victor N OdinokovAbstract:Abstract 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.
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Stereospecific 7α-alkylation of 20-Hydroxyecdysone in a lithium-ammonia solution.
Steroids, 2015Co-Authors: I V Galyautdinov, Zarema R Khairullina, Valery P Sametov, Z. S. Muslimov, Leonard M. Khalilov, Elvira R. Zaripova, Ekaterina S. Mescheryakova, Oleg S. Mozgovoi, Victor N OdinokovAbstract: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.
