Molecular Rearrangements under Chemical Transformations of Ecdysteroids
V. N. ODINOKOV
Institute of Petrochemistry and Catalysis, Ufa Scientific Centre of the Russian Academy of Sciences,
Pr. Oktyabrya 141, Ufa 450075 (Russia)
odinokov@anrb.ru
Keywords: ecdysteroids, 9О±,14О±-epoxy-14О±-desoxyecdysteroids, molecular rearrangements, 9О±,13О±-epoxy-14ОІ-methyl-13ОІ-demethyl-14О±-desoxyecdysteroids, hydride reduction, catalytic hydrogenation
Pages: 633–638
Abstract
It was established that 9α,14α-epoxy-14α-desoxyecdysteroids (oxetanoecdysteroids) formed from the corresponding ecdysteroids in the solutions of alkaline metals in liquid ammonia undergo molecular rearrangements catalyzed by acids. As a result of these rearrangements, 9α,13α-epoxy-14β-methyl-13β-demethyl-14α-desoxyecdysteroids and 9α-hydroxystachisteron В are formed. The reduction of oxetanoecdysteroids by sodium borohydride results not only in the reduction of 6-keto group but also in the rearrangement of the oxetane cycle. The oxetane molecular rearrangement also takes place during catalytic hdyration of Δ 7-bond in oxetanoecdysteroids.
UDC 547+544
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