Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids

In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic ana...

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Autores principales:	Acebedo, S.L., Alonso, F., Ramírez, J.A., Galagovsky, L.R.
Formato:	JOUR
Materias:	A-ring Aromatic stigmastanes Bioactivity Brassinosteroids 19 acetoxystigmasta 4,22 dien 3,6 dione 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one 19 norstigmasta 1(10),5,22 trien 3b ol 19 norstigmasta 1,3,5(10) triene 3,22,23 triol 19 norstigmasta 1,3,5(10),22 tetraen 3 ol 3 hydroxystigmastane 3beta acetoxy 19 norstigmasta 1(10),5,22 triene 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol 3beta acetoxy 5beta,6beta epoxystigmast 22 ene 3beta acetoxystigmasta 5,22 dien 19 ol 3beta,19 diacetoxystigmasta 5,22 diene 9 acetoxystigmasta 5,22 dien 3beta ol 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one aromatic compound brassinosteroid stigmasta 1,4,22 trien 3 one stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone) stigmasterol unclassified drug aromatization article demethylation drug activity hydrolysis oxidation priority journal proton nuclear magnetic resonance stereochemistry synthesis
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00404020_v68_n19_p3685_Acebedo
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_00404020_v68_n19_p3685_Acebedo2023-10-03T14:50:45Z Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids Acebedo, S.L. Alonso, F. Ramírez, J.A. Galagovsky, L.R. A-ring Aromatic stigmastanes Bioactivity Brassinosteroids 19 acetoxystigmasta 4,22 dien 3,6 dione 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one 19 norstigmasta 1(10),5,22 trien 3b ol 19 norstigmasta 1,3,5(10) triene 3,22,23 triol 19 norstigmasta 1,3,5(10),22 tetraen 3 ol 3 hydroxystigmastane 3beta acetoxy 19 norstigmasta 1(10),5,22 triene 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol 3beta acetoxy 5beta,6beta epoxystigmast 22 ene 3beta acetoxystigmasta 5,22 dien 19 ol 3beta,19 diacetoxystigmasta 5,22 diene 9 acetoxystigmasta 5,22 dien 3beta ol 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one aromatic compound brassinosteroid stigmasta 1,4,22 trien 3 one stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone) stigmasterol unclassified drug aromatization article demethylation drug activity hydrolysis oxidation priority journal proton nuclear magnetic resonance stereochemistry synthesis In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic analogs showed a reduced but significant bioactivity when compared to the natural hormones. © 2012 Elsevier Ltd. All rights reserved. Fil:Acebedo, S.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v68_n19_p3685_Acebedo
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	A-ring Aromatic stigmastanes Bioactivity Brassinosteroids 19 acetoxystigmasta 4,22 dien 3,6 dione 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one 19 norstigmasta 1(10),5,22 trien 3b ol 19 norstigmasta 1,3,5(10) triene 3,22,23 triol 19 norstigmasta 1,3,5(10),22 tetraen 3 ol 3 hydroxystigmastane 3beta acetoxy 19 norstigmasta 1(10),5,22 triene 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol 3beta acetoxy 5beta,6beta epoxystigmast 22 ene 3beta acetoxystigmasta 5,22 dien 19 ol 3beta,19 diacetoxystigmasta 5,22 diene 9 acetoxystigmasta 5,22 dien 3beta ol 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one aromatic compound brassinosteroid stigmasta 1,4,22 trien 3 one stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone) stigmasterol unclassified drug aromatization article demethylation drug activity hydrolysis oxidation priority journal proton nuclear magnetic resonance stereochemistry synthesis
spellingShingle	A-ring Aromatic stigmastanes Bioactivity Brassinosteroids 19 acetoxystigmasta 4,22 dien 3,6 dione 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one 19 norstigmasta 1(10),5,22 trien 3b ol 19 norstigmasta 1,3,5(10) triene 3,22,23 triol 19 norstigmasta 1,3,5(10),22 tetraen 3 ol 3 hydroxystigmastane 3beta acetoxy 19 norstigmasta 1(10),5,22 triene 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol 3beta acetoxy 5beta,6beta epoxystigmast 22 ene 3beta acetoxystigmasta 5,22 dien 19 ol 3beta,19 diacetoxystigmasta 5,22 diene 9 acetoxystigmasta 5,22 dien 3beta ol 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one aromatic compound brassinosteroid stigmasta 1,4,22 trien 3 one stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone) stigmasterol unclassified drug aromatization article demethylation drug activity hydrolysis oxidation priority journal proton nuclear magnetic resonance stereochemistry synthesis Acebedo, S.L. Alonso, F. Ramírez, J.A. Galagovsky, L.R. Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
topic_facet	A-ring Aromatic stigmastanes Bioactivity Brassinosteroids 19 acetoxystigmasta 4,22 dien 3,6 dione 19 nor 3,22,23 trihydroxystigmasta 1,3,5(10) triene 6 one 19 norstigmasta 1(10),5,22 trien 3b ol 19 norstigmasta 1,3,5(10) triene 3,22,23 triol 19 norstigmasta 1,3,5(10),22 tetraen 3 ol 3 hydroxystigmastane 3beta acetoxy 19 norstigmasta 1(10),5,22 triene 3beta acetoxy 5alpha bromo 6,19 epoxystigmast 22 ene 3beta acetoxy 5alpha bromostigmast 22 en 6beta ol 3beta acetoxy 5beta,6beta epoxystigmast 22 ene 3beta acetoxystigmasta 5,22 dien 19 ol 3beta,19 diacetoxystigmasta 5,22 diene 9 acetoxystigmasta 5,22 dien 3beta ol 9 nor 3 hydroxystigmasta 1,3,5(10),22 tetraen 6 one aromatic compound brassinosteroid stigmasta 1,4,22 trien 3 one stigmasta 3beta,22,23 triol (6 deoxo 28 homoteasterone) stigmasterol unclassified drug aromatization article demethylation drug activity hydrolysis oxidation priority journal proton nuclear magnetic resonance stereochemistry synthesis
description	In this paper, we report the first synthesis of aromatic analogs of brassinosteroids. In order to accomplish this task, we explored two different synthetic approaches, which involved demethylation of the C-19 of stigmasterol to yield A-ring aromatic 3-hydroxystigmastanes. One of the new aromatic analogs showed a reduced but significant bioactivity when compared to the natural hormones. © 2012 Elsevier Ltd. All rights reserved.
format	JOUR
author	Acebedo, S.L. Alonso, F. Ramírez, J.A. Galagovsky, L.R.
author_facet	Acebedo, S.L. Alonso, F. Ramírez, J.A. Galagovsky, L.R.
author_sort	Acebedo, S.L.
title	Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
title_short	Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
title_full	Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
title_fullStr	Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
title_full_unstemmed	Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids
title_sort	synthesis of aromatic stigmastanes: application to the synthesis of aromatic analogs of brassinosteroids
url	http://hdl.handle.net/20.500.12110/paper_00404020_v68_n19_p3685_Acebedo
work_keys_str_mv	AT acebedosl synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids AT alonsof synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids AT ramirezja synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids AT galagovskylr synthesisofaromaticstigmastanesapplicationtothesynthesisofaromaticanalogsofbrassinosteroids
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Synthesis of aromatic stigmastanes: Application to the synthesis of aromatic analogs of brassinosteroids

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