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Laroche B, Bouvarel T, Louis-Sylvestre M, et al. Diversity-oriented synthesis of 17-spirosteroids. Beilstein J Org Chem. 2020;16:880-887doi: 10.3762/bjoc.16.79.
Laroche, B., Bouvarel, T., Louis-Sylvestre, M., & Nay, B. (2020). Diversity-oriented synthesis of 17-spirosteroids. Beilstein journal of organic chemistry, 16880-887. https://doi.org/10.3762/bjoc.16.79
Laroche, Benjamin, et al. "Diversity-oriented synthesis of 17-spirosteroids." Beilstein journal of organic chemistry vol. 16 (2020): 880-887. doi: https://doi.org/10.3762/bjoc.16.79
Laroche B, Bouvarel T, Louis-Sylvestre M, Nay B. Diversity-oriented synthesis of 17-spirosteroids. Beilstein J Org Chem. 2020 Apr 28;16:880-887. doi: 10.3762/bjoc.16.79. eCollection 2020. PMID: 32461769; PMCID: PMC7214869.
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Beilstein J Org Chem. 2020 Apr 28;16:880-887. doi: 10.3762/bjoc.16.79. eCollection 2020.

Diversity-oriented synthesis of 17-spirosteroids.

Beilstein journal of organic chemistry

Benjamin Laroche, Thomas Bouvarel, Martin Louis-Sylvestre, Bastien Nay

Affiliations

  1. Unité Molécules de Communication et Adaptations des Micro-organismes (MCAM), Muséum National d'Histoire Naturelle, CNRS, Paris, France.
  2. Laboratoire de Synthèse Organique, Ecole Polytechnique, CNRS, ENSTA, Institut Polytechnique de Paris, Palaiseau Cedex, France.

PMID: 32461769 PMCID: PMC7214869 DOI: 10.3762/bjoc.16.79

Abstract

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.

Copyright © 2020, Laroche et al.; licensee Beilstein-Institut.

Keywords: 17-ethynyl-17-hydroxysteroids; diversity-oriented strategy; ring-closing enyne metathesis; spirosteroids; steroids

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