22-氧代-23-螺缩酮的区域选择性裂解。具有侧链上吡喃酮和环戊烯酮 E 环的新型胆甾烷骨架。
Regioselective cleavage of 22-oxo-23-spiroketals. Novel cholestanic frameworks with pyranone and cyclopentenone E rings on the side chain.
机构信息
Instituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Ed.B-1, C.U., Morelia, Michoacán 58030, Mexico.
出版信息
Steroids. 2012 Apr;77(5):534-41. doi: 10.1016/j.steroids.2012.01.018. Epub 2012 Feb 8.
The regioselective opening of the F ring of 22-oxo-23-spiroketals using a saturated solution of HCl in acetic anhydride yielded novel cholestanic frameworks with pyranone or cyclopentenone E rings. The structures of the new derivatives of sarsasapogenin, diosgenin and hecogenin thus obtained were established using one and two dimensional (1)H, (13)C experiments (DEPT, COSY, HETCOR, HMBC, ROESY, and NOESY). The X-ray analysis for compound 11b confirmed the 23R configuration for the new stereogenic center.
用乙酸酐中饱和的 HCl 溶液选择性地打开 22-氧代-23-螺缩酮的 F 环，得到了具有吡喃酮或环戊烯酮 E 环的新型胆甾烷骨架。使用一维和二维（1）H、（13）C 实验（DEPT、COSY、HETCOR、HMBC、ROESY 和 NOESY）确定了由此获得的薯蓣皂素、孕烷和海柯皂素新衍生物的结构。化合物 11b 的 X 射线分析证实了新的立体中心为 23R 构型。
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