坎利酮的简便高效合成法

Facile and Highly Efficient Synthesis of Canrenone

关键词:  醋酸去氢表雄酮  2,3-二氯-5,6-二氰基-1,4-苯醌  坎利酮  α,β-不饱和羰基甾体  螺环羧内酯

Key words:  dehydroepiandrosterone acetate  2,3-dichloro-5,6-dicyano-1,4-benzoquinone  canrenone  α,β-unsaturated carbonyl steroid  spiro-carbolactone

摘要:

目的 简便高效合成坎利酮。方法 将醋酸去氢表雄酮依次经硫叶立德环氧化，NaCH(COOEt)2内酯化，2,3-二氯-5,6-二氰基-1,4-苯醌选择性脱氢得到目标产物坎利酮。结果 总产率69.8%。目标物经紫外光谱、红外光谱、核磁共振氢谱、质谱及元素分析确证了其化学结构。结论　改进后的工艺原材料价廉易得，操作简便，降低了生产成本，更适合工业化生产。

Abstract:

OBJECTIVE To improve the synthetic procedure of canrenone. METHODS Canrenone was conveniently and high effectively synthesized from dehydroepiandrosterone acetate via epoxidation with sulfur ylide, carbolactonization with NaCH(COOEt)2, and regioselective dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, in sequence. RESULTS The total yield of canrenone was up to 69.8%. The chemical structures of target product were characterized by UV, IR, 1H-NMR, MS, and element analysis. CONCLUSION The improved procedure avoids the use of expensive reagents and canrenone was synthesized in a convenient way, which is facile for scale production.