Concise and Straightforward Asymmetric Synthesis of a Cyclic Natural Hydroxy-Amino Acid

被引：1

作者：

Simirgiotis, Mario J. ^{[1
]}

Vallejos, Javier ^{[2
]}

Areche, Carlos ^{[3
]}

Sepulveda, Beatriz ^{[4
]}

机构：

[1] Univ Antofagasta, Fac Ciencias Basicas, Lab Prod Nat, Antofagasta 1240000, Chile

[2] Univ Catolica Norte, Dept Quim, Antofagasta 1240000, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago 7800024, Chile

[4] Univ Andres Bello, Dept Ciencias Quim, Vina Del Mar 2520000, Chile

来源：

MOLECULES | 2014年 / 19卷 / 12期

关键词：

pipecolic acid; total synthesis; piperidine; amino acids; PROTEASE INHIBITORS; DERIVATIVES; 1-DEOXYGALACTONOJIRIMYCIN; ANALOGS; SEEDS;

D O I：

10.3390/molecules191219516

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An enantioselective total synthesis of the natural amino acid (2S,4R,5R)-4,5-di-hydroxy-pipecolic acid starting from D-glucoheptono-1, 4-lactone is presented. The best sequence employed as a key step the intramolecular nucleophilic displacement by an amino function of a 6-O-p-toluene-sulphonyl derivative of a methyl D-arabino-hexonate and involved only 12 steps with an overall yield of 19%. The structures of the compounds synthesized were elucidated on the basis of comprehensive spectroscopic (NMR and MS) and computational analysis.

引用

页码：19516 / 19531

页数：16

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