Synthesis of C(1)-C(11) oxygen-bridged pregnanes

A general procedure for the synthesis of 1α,11α- and 1β,11α-epoxysteroids is described, using an intramolecular remote functionalization reaction involving the photolysis of 11α-hydroxysteroids in the presence of diacetoxyiodobenzene and iodine. Three 1,11-epoxypregnanes were prepared, two of them (compounds 10 and 14) are conformationally constrained analogues of steroidal hormones, compound 13 is a synthetic precursor of neurosteroids.

Palabras clave: 1,11-EPOXYPREGNANE , DIACETOXYIODOBENZENE , DIB , REMOTE FUNCTIONALIZATION REACTION , STEROID

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Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)

Identificadores

URI: http://hdl.handle.net/11336/85341

URL: https://www.sciencedirect.com/science/article/pii/S0040403905008592

DOI: https://doi.org/10.1016/j.tetlet.2005.04.052

Colecciones

Articulos(IFIBYNE)
Articulos de INST.DE FISIOL., BIOL.MOLECULAR Y NEUROCIENCIAS

Articulos(UMYMFOR)
Articulos de UNID.MICROANAL.Y MET.FISICOS EN QUIM.ORG.(I)

Citación

Veleiro, Adriana Silvia; Taich, Paula Juliana; Alvarez, Lautaro Damian; Di Chenna, Pablo Hector; Burton, Gerardo; Synthesis of C(1)-C(11) oxygen-bridged pregnanes; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 46; 24; 6-2005; 4235-4238

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