Asymmetric Synthesis of Homocitric Acid Lactone

被引：8

作者：

Nickerson, Leslie A. ^{[1
]}

Huynh, Valerie ^{[1
]}

Balmond, Edward I. ^{[1
]}

Cramer, Stephen P. ^{[1
]}

Shaw, Jared T. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, One Shields Ave, Davis, CA 95616 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

关键词：

ACETATE ALDOL ADDITIONS; ACETYL THIAZOLIDINETHIONE REAGENT; IRON-MOLYBDENUM COFACTOR; ENANTIOSELECTIVE SYNTHESIS; CHIRAL AUXILIARY; GAMMA-LACTONE; NITROGENASE; IDENTIFICATION; RESOLUTION; ALDEHYDES;

D O I：

10.1021/acs.joc.6b01997

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short, diastereoselective synthesis of homocitric acid lactone is described. The key step is a bioinspired aldol addition to set the stereogenic center in an intermediate that requires only modest oxidation state manipulation to complete the synthesis. This approach enables rapid generation of isotopomers in which carbon and hydrogen can be replaced by heavier nuclei at nearly every position.

引用

页码：11404 / 11408

页数：5

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