Abstract
AbstractA novel and efficient synthetic strategy to access unique C‐2 substituted steroid analogues 3 and 4 is described. The unusual C‐2 aryl ether analogues 3 were shown to act as virtual antagonists of LRH‐1 and were prepared as single diastereoisomers, employing a fifteen‐step sequence from pregnenolone (9). The key steps include the stereoconvergent nucleophilic displacement of an epimeric mixture of 3‐keto 2‐bromo steroids, chemoselective carbonylation of an enol triflate and conversion of a thiopyridyl ester into an aryl ketone. The related C‐2 benzyl analogues 4 were prepared in a similar manner.
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