Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII.* synthesis of ω-carboxy derivatives of 20-hydroxyecdysone diacetonide

被引：2
|
作者：
Savchenko, R. G. [1 ]
Urazaeva, Ya. R. [1 ]
Kostyleva, S. A. [1 ]
Odinokov, V. N. [1 ]
机构：
[1] Russian Acad Sci, Inst Petrochem & Catalysis, Ufa 450075, Bashkortostan, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 49卷 / 04期
关键词：
Ozone; Ozonolysis; Diazomethane; Malonic Acid; Compound VIII;
D O I：
10.1134/S1070428013040192
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ozonolysis of omega-anhydro-20-hydroxyecdysone diacetonide gave a mixture of 24- and 25-oxo derivatives, and only the first of these (23-carbaldehyde) reacted with malonic acid according to Knoevenagel to give 14 alpha-hydroxy-2 beta,3 beta: 20,22-bis(isopropylidenedioxy)-6-oxo-27-nor-5 beta-cholesta-7,24-dien-26-oic acid. The oxidation of 23-carbaldehyde with ozone, followed by treatment with diazomethane, afforded 20-hydroxy-25,26,27-trinorecdysone-23-carboxylic acid methyl ester diacetonide.
引用
收藏
页码：610 / 613
页数：4
相关论文
共 50 条
  • [1] Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII.* synthesis of ω-carboxy derivatives of 20-hydroxyecdysone diacetonide
    R. G. Savchenko
    Ya. R. Urazaeva
    S. A. Kostyleva
    V. N. Odinokov
    Russian Journal of Organic Chemistry, 2013, 49 : 610 - 613
  • [2] Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride
    G. Yu. Ishmuratov
    A. Kh. Shayakhmetova
    M. P. Yakovleva
    Yu. V. Legostaeva
    O. V. Shitikova
    E. G. Galkin
    G. A. Tolstikov
    Russian Journal of Organic Chemistry, 2007, 43 : 1114 - 1119
  • [3] Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride
    Ishmuratov, G. Yu.
    Shayakhmetova, A. Kh.
    Yakovleva, M. P.
    Legostaeva, Yu. V.
    Shitikova, O. V.
    Galkin, E. G.
    Tolstikov, G. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 43 (08) : 1114 - 1119
  • [4] Synthesis of 20-hydroxyecdysone oxime, its diacetonide, and their 14,15-anhydro derivatives
    Galyautdinov, I. V.
    Ves'kina, N. A.
    Afon'kina, S. R.
    Khalilov, L. M.
    Odinokov, V. N.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (09) : 1333 - 1339
  • [5] OZONOLYSIS OF ALKENES AND STUDY OF REACTIONS OF POLYFUNCTIONAL COMPOUNDS .49. SYNTHESIS OF ACYLPRENOL CHLORINE-DERIVATIVES
    ODINOKOV, VN
    KUKOVINETS, OS
    SAKHAROVA, NI
    TOLSTIKOV, GA
    ZHURNAL ORGANICHESKOI KHIMII, 1992, 28 (07): : 1346 - 1351
  • [6] Synthesis of 20-hydroxyecdysone oxime, its diacetonide, and their 14,15-anhydro derivatives
    I. V. Galyautdinov
    N. A. Ves’kina
    S. R. Afon’kina
    L. M. Khalilov
    V. N. Odinokov
    Russian Journal of Organic Chemistry, 2006, 42 : 1333 - 1339
  • [7] Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVII. Synthesis of 27,27,27-trifluoro-20-hydroxyecdysone acetonides from 24,25- and 25,26-anhydro-20-hydroxyecdysone derivatives via ozonolysis and trifluoromethylation
    Odinokov, VN
    Savchenko, RG
    Afon'kina, R
    Khalilov, LM
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 41 (03) : 376 - 385
  • [8] Ozonolysis of Alkenes and Study of Reactions of Polyfunctional Compounds: LXVII. Synthesis of 27,27,27-Trifluoro-20-hydroxyecdysone Acetonides from 24,25- and 25,26-Anhydro-20-hydroxyecdysone Derivatives via Ozonolysis and Trifluoromethylation
    V. N. Odinokov
    R. G. Savchenko
    S. R. Afon’kina
    L. M. Khalilov
    Russian Journal of Organic Chemistry, 2005, 41 : 376 - 385
  • [9] OZONOLYSIS OF ALKENES AND STUDY OF REACTIONS OF POLYFUNCTIONAL COMPOUNDS .41. SYNTHESIS OF OXYGEN-CONTAINING TRIACONTANE DERIVATIVES
    ODINOKOV, VN
    AKHMETOVA, VR
    KHASANOV, KD
    ABDUVAKHABOV, AA
    TOLSTIKOV, GA
    ZHURNAL ORGANICHESKOI KHIMII, 1990, 26 (07): : 1402 - 1404
  • [10] Ozonolysis of alkenes and study of the reactions of polyfunctional compounds - LX. Ozonolysis of dihydroderived aromatic compounds
    Kukovinets, OS
    Kasradze, VG
    Akhmetova, VR
    Zainullin, RA
    Bazylchik, V
    Fedorov, PI
    Abdullin, MI
    Odinokov, VN
    Galin, FZ
    Tolstikov, GA
    ZHURNAL ORGANICHESKOI KHIMII, 1999, 35 (05): : 728 - 731
12345