Diversity-oriented synthesis of 17-spirosteroids

被引：1

作者：

Laroche, Benjamin ^{[1
]}

Bouvarel, Thomas ^{[1
]}

Louis-Sylvestre, Martin ^{[2
]}

Nay, Bastien ^{[1
,2
]}

机构：

[1] CNRS, Museum Natl Hist Nat, Unite Mol Commun & Adaptat Microorganismes MCAM, Paris, France

[2] Inst Polytech Paris, ENSTA, CNRS, Lab Synthese Organ,Ecole Polytech, Palaiseau, France

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 16卷

关键词：

diversity-oriented strategy; 17-ethynyl-17-hydroxysteroids; ring-closing enyne metathesis; spirosteroids; steroids; METATHESIS/DIELS-ALDER REACTION; ENYNE METATHESIS; NATURAL-PRODUCTS; RING-DISTORTION; SKELETAL DIVERSITY; SPIRO-STEROIDS; STEREOCHEMICALLY COMPLEX; PRIVILEGED STRUCTURES; STRATEGY; COLLECTION;

D O I：

10.3762/bjoc.16.79

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：880 / 887

页数：8

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