Sonochemically assisted 2,3-dideoxygenation and skeletal rearrangement of ecdysteroid derivatives.
Ultrason Sonochem
; 52: 505-511, 2019 Apr.
Article
em En
| MEDLINE
| ID: mdl-30594517
ABSTRACT
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-Δ2(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 C13-C14 bond migration with C/D rings contraction/expansion and providing novel short chain (8R)-13(14â¯ââ¯8)-abeo-isomer.
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MEDLINE
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article