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 (...

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Detalles Bibliográficos
Autores principales:	Veleiro, Adriana Silvia, Alvarez, Lautaro Damián, Di Chenna, Pablo Héctor, Burton, Gerardo
Publicado:	2005
Materias:	1,11-Epoxypregnane Diacetoxyiodobenzene DIB Remote functionalization reaction Steroid hydroxysteroid iodine iodobenzene pregnane derivative steroid hormone article chemical reaction kinetics drug conformation drug synthesis photolysis
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v46_n24_p4235_Veleiro http://hdl.handle.net/20.500.12110/paper_00404039_v46_n24_p4235_Veleiro
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404039_v46_n24_p4235_Veleiro
record_format	dspace
spelling	paper:paper_00404039_v46_n24_p4235_Veleiro2023-06-08T15:04:27Z Synthesis of C(1)-C(11) oxygen-bridged pregnanes Veleiro, Adriana Silvia Alvarez, Lautaro Damián Di Chenna, Pablo Héctor Burton, Gerardo 1,11-Epoxypregnane Diacetoxyiodobenzene DIB Remote functionalization reaction Steroid hydroxysteroid iodine iodobenzene pregnane derivative steroid hormone article chemical reaction kinetics drug conformation drug synthesis photolysis 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. © 2005 Elsevier Ltd. All rights reserved. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Alvarez, L.D. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Di Chenna, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v46_n24_p4235_Veleiro http://hdl.handle.net/20.500.12110/paper_00404039_v46_n24_p4235_Veleiro
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	1,11-Epoxypregnane Diacetoxyiodobenzene DIB Remote functionalization reaction Steroid hydroxysteroid iodine iodobenzene pregnane derivative steroid hormone article chemical reaction kinetics drug conformation drug synthesis photolysis
spellingShingle	1,11-Epoxypregnane Diacetoxyiodobenzene DIB Remote functionalization reaction Steroid hydroxysteroid iodine iodobenzene pregnane derivative steroid hormone article chemical reaction kinetics drug conformation drug synthesis photolysis Veleiro, Adriana Silvia Alvarez, Lautaro Damián Di Chenna, Pablo Héctor Burton, Gerardo Synthesis of C(1)-C(11) oxygen-bridged pregnanes
topic_facet	1,11-Epoxypregnane Diacetoxyiodobenzene DIB Remote functionalization reaction Steroid hydroxysteroid iodine iodobenzene pregnane derivative steroid hormone article chemical reaction kinetics drug conformation drug synthesis photolysis
description	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. © 2005 Elsevier Ltd. All rights reserved.
author	Veleiro, Adriana Silvia Alvarez, Lautaro Damián Di Chenna, Pablo Héctor Burton, Gerardo
author_facet	Veleiro, Adriana Silvia Alvarez, Lautaro Damián Di Chenna, Pablo Héctor Burton, Gerardo
author_sort	Veleiro, Adriana Silvia
title	Synthesis of C(1)-C(11) oxygen-bridged pregnanes
title_short	Synthesis of C(1)-C(11) oxygen-bridged pregnanes
title_full	Synthesis of C(1)-C(11) oxygen-bridged pregnanes
title_fullStr	Synthesis of C(1)-C(11) oxygen-bridged pregnanes
title_full_unstemmed	Synthesis of C(1)-C(11) oxygen-bridged pregnanes
title_sort	synthesis of c(1)-c(11) oxygen-bridged pregnanes
publishDate	2005
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v46_n24_p4235_Veleiro http://hdl.handle.net/20.500.12110/paper_00404039_v46_n24_p4235_Veleiro
work_keys_str_mv	AT veleiroadrianasilvia synthesisofc1c11oxygenbridgedpregnanes AT alvarezlautarodamian synthesisofc1c11oxygenbridgedpregnanes AT dichennapablohector synthesisofc1c11oxygenbridgedpregnanes AT burtongerardo synthesisofc1c11oxygenbridgedpregnanes
_version_	1768546575356788736

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

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