Аннотация:
9α,14α-Epoxy-14-deoxy-20-hydroxyecdysone diacetonide on treatment with NaBH4 undergoes reduction of 6-keto group and cleavage of allylic oxetane ring, the 6-keto reduction is accompanied by β→α epimerization of the adjacent HC5 centre. Subsequent re-oxidation of the 6-CHOH fragment into ketone with pyridinium chlorochromate and acidic deprotection affords 25-hydroxydachryhainansterone possessing β-HC5 configuration due to the re-epimerisation at this centre.
Образец цитирования:
N. A. Veskina, A. Sh. Ibragimova, I. V. Galyautdinov, L. M. Khalilov, V. N. Odinokov, “Transformation of 9α,14α-epoxy-14-deoxy-20-hydroxyecdysone diacetonide into 25-hydroxydachryhainansterone”, Mendeleev Commun., 20:5 (2010), 293–295
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc3071
https://www.mathnet.ru/rus/mendc/v20/i5/p293
Эта публикация цитируется в следующих 7 статьяx:
D. N. Olennikov, “Makisterone C-20,22-Acetonide from Rhaponticum uniflorum”, Chem Nat Compd, 54:5 (2018), 930
R. G. Savchenko, Ya. R. Urazaeva, S. A. Kostyleva, V. N. Odinokov, “Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII.* synthesis of ω-carboxy derivatives of 20-hydroxyecdysone diacetonide”, Russ J Org Chem, 49:4 (2013), 610
V. N. Odinokov, “Synthesis of natural ecdysteroids and structural analogs by chemical transformations of available phytoecdysteroids”, Russ Chem Bull, 61:7 (2012), 1391
N. A. Ves'kina, V. N. Odinokov, “Transformations of ecdysteroids in the synthesis of their structural analogs and minor phytoecdysteroids”, Russ J Org Chem, 48:9 (2012), 1137
S. R. Afon'kina, R. G. Savchenko, N. A. Ves'kina, I. V. Galyautdinov, V. N. Odinokov, “9α-hydroxylation of 25-fluoroponasterone a diacetonide in lithium-ammonia solution”, Russ J Org Chem, 48:3 (2012), 463
Rimma G. Savchenko, Yana R. Urasaeva, Ilgiz V. Galyautdinov, Svetlana R. Afonkina, Leonard M. Khalilov, Fedor M. Dolgushin, Victor N. Odinokov, “Synthesis of 7,8α-dihydro-14α-deoxyecdysteroids”, Steroids, 76:6 (2011), 603
N. A. Ves'kina, S. R. Afon'kina, V. N. Odinokov, “Stereospecific formation of 7,8β-dihydroanalogs at the reduction of ponasterone acetonide with lithium in liquid ammonia”, Russ J Org Chem, 47:11 (2011), 1767
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