title: 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.
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.
authors.affiliation: 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.
authors.forename: Ilgiz V
authors.initials: IV
authors.lastname: Galyautdinov
authors.affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
authors.forename: Zarema R
authors.initials: ZR
authors.lastname: Khairullina
authors.affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
authors.forename: Valery P
authors.initials: VP
authors.lastname: Sametov
authors.affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
authors.forename: Zabir S
authors.initials: ZS
authors.lastname: Muslimov
authors.affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
authors.forename: Leonard M
authors.initials: LM
authors.lastname: Khalilov
authors.affiliation: Institute of Petrochemistry and Catalysis, Russian Academy of Sciences, Laboratory of Organic Synthesis, Prospect Oktyabrya 141, 450075 Ufa, Russian Federation.
authors.forename: Victor N
authors.initials: VN
authors.lastname: Odinokov
mesh_terms: D000478:Alkylation; D004441:Ecdysterone / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D004441:Ecdysterone; D010293:Pargyline; C458239:propargyl bromide
keywords: 20-Hydroxyecdysone; Alkylation; Bis-alkylation; Lithium–ammonia solution; Propargyl bromide; Spirocyclization