Highly Stereocontrolled and Regiocontrolled Syntheses of 2,3,4-Trisubstituted Alkanoates and Lactones

[摘要]：New chlorodiols (+/-)-3 and (+/-)-5 are densely functionalized and versatile synthons. They are converted in one step on a gram scale into 2-chlorolactones (+/-)-6 and (+/-)-7 and into 4-hydroxy glycidate esters (+/-)-9 and (+/-)-10. The 4-hydroxy glycidate esters (+/-)-9 and (+/-)-10 are converted stereospecifically and regiospecifically into oxazolines (+/-)-13 and (+/-)-14 and into cyclic carbamates (+/-)-18 (+/-)-20. The 4-hydroxy glycidate ester (+/-)-10 undergoes stereocontrolled and regiocontrolled epoxide opening by sodium azide to form the 2-azido-3,4-dihydroxy alkanoate (+/-)-21. Finally, chlorodiol (+/-)-5 reacts stereospecifically with silver triflate to form the 2,3-dihydroxyfuranone (+/-)-26.

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