Beilstein J. Org. Chem.2020,16, 880–887, doi:10.3762/bjoc.16.79
Paris, Palaiseau Cedex, France 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.
Keywords: diversity-oriented strategy; 17-ethynyl-17-hydroxysteroids
targeted strategy, lies on the 17-ethynyl-17-hydroxysteroids (Figure 1). They are commonly used as contraceptive while their skeleton is structurally diversified, especially at ring A. They are thus synthetically relevant as starting materials in a DOS approach. Indeed, after installing an alkenyl ether on
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Graphical Abstract
Scheme 1:
Two diversity-oriented strategies: (a) Diversity installed during the construction of the skeleton;...