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

被引：6

作者：

Hencken, Christopher P. ^{[1
]}

Genna, Douglas T. ^{[1
]}

Siegler, Maxime A. ^{[1
]}

Posner, Gary H. ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 12期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; ENANTIOSELECTIVE SYNTHESES; GAMMA-BUTYROLACTONES; 2,3-EPOXY ALCOHOLS; NATURAL-PRODUCTS; GLYCOLIC ACID; ESTERS; EFFICIENT; ALPHA; PHYTOSPHINGOSINE;

D O I：

10.1021/jo200795f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：5149 / 5155

页数：7

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