Ginanneschi M, Chelli M, Papini A, Rapi G
Cattedra di Chimica Medica, Facoltà di Medicina e Chirurgia, Florence, Italy.
Steroids. 1990 Nov;55(11):501-6. doi: 10.1016/0039-128x(90)90088-s.
Spiro[androst-4-en-17 alpha,5'-oxazolidine]-2',3,4'-trione 8a and spiro[androst-4-en-17 alpha,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 17 alpha-hydroxy-17-carboxyesters and 17 alpha-hydroxy-17-carboxamides is described. Attempts to synthesize the title compounds from these products were unsuccessful.
螺[雄甾-4-烯-17α,5'-恶唑烷]-2',3,4'-三酮8a和螺[雄甾-4-烯-17α,5'-恶唑烷]-2',3,4',11-四酮8b这两种具有潜在生物活性的螺环化合物，由母体17-酮经四步反应制得（产率分别为64%和49.5%）。关键中间体是羟基亚氨酸酯5a和5b，用氯代碳酸烷基酯处理时，它们很容易环化生成相应的螺恶唑啉酮4'-烯醇醚。在KF存在下，用正戊基溴得到螺环化合物8a和8b各自的N-戊基衍生物。描述了一种合成甾体17α-羟基-17-羧酸酯和17α-羟基-17-羧酰胺的新方法。尝试从这些产物合成标题化合物未成功。
