Highly efficient synthesis of steroid-17-spiro-5'-oxazolidine-2', 4' -diones from 17-keto steroids

Add time:08/19/2019    Source:sciencedirect.com

Spiro[androst-4-en-17α,5'-oxazolidine]-2',3,4'-trione 8a and spiro[androst-4-en-17α,5'-oxazolidine]-2', 3,4',11-tetraone 8b, two potentially bioactive spiranes, were prepared from the parent 17-ketones in four steps (64% and 49.5% yield, respectively). The key intermediates were the hydroxyimidates 5a and 5b, which easily underwent cyclization to the corresponding spirooxazolinone 4'-enol ethers when treated with alkylchlorocarbonates. The respective N-amyl derivatives of the spiranes 8a and 8b were obtained with n-pentyl bromide in the presence of KF. A new method for the synthesis of steroid I7αhydroxy-17-carboxyesters and I7α-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful. (Steroids 55:501–506, 1990)

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