Journal of Organic Chemistry p. 3687 - 3691 (1993)
Update date:2022-08-18
Topics:
Stoelwinder, Johannes
Leusen, Albert M. van
The synthesis is described of a series of polyfunctional unsaturated Δ16,20-20-isocyanosteroids 5a-f by the Wittig-Horner-Emmons reaction of (E)-17<(diethylphosphono)isocyanomethylene> steroid 4 with several aldehydes and with acetone.Hydrolysis of the isocyanosteroids 5a-f with dilute sulfuric acid gave Δ16-20-ketosteroids 6a-f in high yield.Hydrolysis of 5a was also possible under neutral conditions, via the intermediate Δ16,20-20-isocyanatosteroid 7a, leading to A-ring protected 16-dehydroprogesterone 8a.The Wittig-Horner-Emmons reaction, together with the described hydrolyses, provides a new method for the introduction of steroid side chains.The method is particularly suited for side chains of different size, structure, and functionality.
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