Abstract

The Michael adducts of levoglucosenone and cyclohexanone were used to develop a rapid synthesis of nonano-9-lactones fused to a pyran ring containing a pharmacophoric dichloromethylene substituent. The key step in the synthesis is a cleavage, under the action of pyridinium chlorochromate, of the bridge in the hexahydrochroman formed by the etherification of the keto function by the hydroxyl group in the 1,6-anhydro bridge, which accompanies the cleavage the latter bridge in the levoglucosenone–cyclohexanone Michael adduct. It was established that the presence of the dichloromethylene substituent in the pyran ring does not significantly affect the cleavage of the hexahydrochroman bridge.

中文翻译：

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壬基-9-内酯与含二氯亚甲基取代基的吡喃环的合成

摘要

左葡糖酮和环己酮的迈克尔加合物被用于快速合成壬基9-内酯，所述壬基9-内酯与含有药效性二氯亚甲基取代基的吡喃环稠合。合成的关键步骤是在氯铬酸吡啶鎓的作用下裂解六氢苯并二氢吡喃中的桥，该桥是由酮官能团被1,6-脱水桥上的羟基醚化而形成的，该裂解伴随着后者的裂解。左葡萄糖葡萄糖酮-环己酮迈克尔加成物中的桥。已经确定，吡喃环中二氯亚甲基取代基的存在不会显着影响六氢苯并二氢吡喃桥的裂解。