title: Stereospecific 7α-alkylation of 20-hydroxyecdysone in a lithium-ammonia solution.
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.
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: Bashkir State University, Zaki Validi Street 32, 450076 Ufa, Russian Federation.
authors.forename: Elvira R
authors.initials: ER
authors.lastname: Zaripova
authors.affiliation: Bashkir State University, Zaki Validi Street 32, 450076 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: Ekaterina S
authors.initials: ES
authors.lastname: Mescheryakova
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: Bashkir State University, Zaki Validi Street 32, 450076 Ufa, Russian Federation.
authors.forename: Oleg S
authors.initials: OS
authors.lastname: Mozgovoi
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; D000641:Ammonia / Q000737:chemistry*; D002384:Catalysis; D004441:Ecdysterone / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*
chemical_list: D004441:Ecdysterone; D000641:Ammonia; D008094:Lithium
keywords: 20-Hydroxyecdysone; 7α-Alkylation; 7α-Methyl-, 7α-ethyl-, 7α-n-propyl-, 7α-allyl-14-deoxy-Δ(8(14))-20-hydroxyecdysone; Lithium–ammonia solution