Diversity-oriented synthesis of 17-spirosteroids

A diversity-oriented synthesis (DOS) approach has been used to functionalize 17-ethynyl-17-hydroxysteroids through a one-pot procedure involving a ring-closing enyne metathesis (RCEYM) and a Diels–Alder reaction on the resulting diene, under microwave irradiations. Taking advantage of the propargyl...

Descripción completa

Detalles Bibliográficos
Autores principales: Laroche, Benjamin, Bouvarel, Thomas, Louis-Sylvestre, Martin, Nay, Bastien
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214869/
https://www.ncbi.nlm.nih.gov/pubmed/32461769
http://dx.doi.org/10.3762/bjoc.16.79
_version_ 1783532063696093184
author Laroche, Benjamin
Bouvarel, Thomas
Louis-Sylvestre, Martin
Nay, Bastien
author_facet Laroche, Benjamin
Bouvarel, Thomas
Louis-Sylvestre, Martin
Nay, Bastien
author_sort Laroche, Benjamin
collection PubMed
description A diversity-oriented synthesis (DOS) approach has been used to functionalize 17-ethynyl-17-hydroxysteroids through a one-pot procedure involving a ring-closing enyne metathesis (RCEYM) and a Diels–Alder reaction on the resulting diene, under microwave irradiations. Taking advantage of the propargyl alcohol moiety present on commercially available steroids, this classical strategy was applied to mestranol and lynestrenol, giving a collection of new complex 17-spirosteroids.
format Online
Article
Text
id pubmed-7214869
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-72148692020-05-26 Diversity-oriented synthesis of 17-spirosteroids Laroche, Benjamin Bouvarel, Thomas Louis-Sylvestre, Martin Nay, Bastien Beilstein J Org Chem Full Research Paper A diversity-oriented synthesis (DOS) approach has been used to functionalize 17-ethynyl-17-hydroxysteroids through a one-pot procedure involving a ring-closing enyne metathesis (RCEYM) and a Diels–Alder reaction on the resulting diene, under microwave irradiations. Taking advantage of the propargyl alcohol moiety present on commercially available steroids, this classical strategy was applied to mestranol and lynestrenol, giving a collection of new complex 17-spirosteroids. Beilstein-Institut 2020-04-28 /pmc/articles/PMC7214869/ /pubmed/32461769 http://dx.doi.org/10.3762/bjoc.16.79 Text en Copyright © 2020, Laroche et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Laroche, Benjamin
Bouvarel, Thomas
Louis-Sylvestre, Martin
Nay, Bastien
Diversity-oriented synthesis of 17-spirosteroids
title Diversity-oriented synthesis of 17-spirosteroids
title_full Diversity-oriented synthesis of 17-spirosteroids
title_fullStr Diversity-oriented synthesis of 17-spirosteroids
title_full_unstemmed Diversity-oriented synthesis of 17-spirosteroids
title_short Diversity-oriented synthesis of 17-spirosteroids
title_sort diversity-oriented synthesis of 17-spirosteroids
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214869/
https://www.ncbi.nlm.nih.gov/pubmed/32461769
http://dx.doi.org/10.3762/bjoc.16.79
work_keys_str_mv AT larochebenjamin diversityorientedsynthesisof17spirosteroids
AT bouvarelthomas diversityorientedsynthesisof17spirosteroids
AT louissylvestremartin diversityorientedsynthesisof17spirosteroids
AT naybastien diversityorientedsynthesisof17spirosteroids

Ejemplares similares