Sonochemically assisted 2,3-dideoxygenation and skeletal rearrangement of ecdysteroid derivatives.

Autor: Savchenko RG; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation. Electronic address: ecdysona@gmail.com., Kostyleva SA; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation., Apaeva AV; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation., Mesheryakova ES; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation., Tukhbatullin AA; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation., Odinokov VN; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation., Parfenova LV; Institute of Petrochemistry and Catalysis of Russian Academy of Sciences, prosp. Oktyabrya 141, 450075 Ufa, Russian Federation.
Jazyk: angličtina
Zdroj: Ultrasonics sonochemistry [Ultrason Sonochem] 2019 Apr; Vol. 52, pp. 505-511. Date of Electronic Publication: 2018 Dec 19.
DOI: 10.1016/j.ultsonch.2018.12.029
Abstrakt: Sonochemical 2,3-dideoxygenation of ecdysteroids with the Δ 2(3) -bond generation and activation of the C-C bonds of the steroid core in the poststerone derivatives, that causes the skeletal rearrangement have been carried out for the first time. Thus, the ultrasonically assisted reaction of 2,3-dimesyloxy derivatives of ecdysteroids with the NaI-Zn-DMF system gives rise to their 2,3-dideoxy-Δ 2(3) -analogues with yields 70-92%. In the case of 2,3-dimesyloxypoststerone as the initial ecdysteroid substrate the reaction is accompanied by the activation of the allyl moiety and semipinacol rearrangement, resulting in the C 13 -C 14 bond migration with C/D rings contraction/expansion and providing novel short chain (8R)-13(14 → 8)-abeo-isomer.
(Copyright © 2018 Elsevier B.V. All rights reserved.)
Databáze: MEDLINE
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