ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A simple and efficient new method for the highly stereoselective (at C (17) and C (20)) introduction of steroid side chains which are suitably functionalized for further elaboration is presented. The ene reaction of (17 Z)-ethylidene steroids, which are readily obtained from 17-keto steroids via a Wittig reaction, with various enophiles such as formaldehyde and acrylate esters leads to useful intermediates which contain the natural steroid configuration at C (20). Catalytic hydrogenation of the Δ16-double bond occurs from the α-face to stereospecifically generate the correct configuration at C (17). An additional chiral center at C (23) is also introduced stereoselectively by the use of methyl 2-chloroacrylate as the enophile.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19810640546
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