Synthesis of All the Diastereomers of 2-Amino-3-hydroxy-4,5-dimethylhexanoic Acid

被引：6

作者：

Spengler, Jan ^{[1
,2
]}

Albericio, Fernando ^{[1
,2
,3
,4
]}

机构：

[1] Inst Res Biomed, Barcelona 08028, Spain

[2] CIBER BBN, Networking Ctr Bioengn Biomat & Nanomed, Barcelona 08028, Spain

[3] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain

[4] Univ KwaZulu Natal, Sch Chem & Phys, ZA-4000 Durban, South Africa

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 01期

关键词：

Amino acids; Asymmetric synthesis; Hydrogenation; Cyclization; CYCLODEPSIPEPTIDES; ANALOGS;

D O I：

10.1002/ejoc.201301257

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe an efficient stereoselective synthesis of all the diastereomers of 2-amino-3-hydroxy-4,5-dimethylhexanoic acid. The -branched carbon skeleton was set up by reaction of Garner's aldehyde with 2-lithio-3-methyl-2-butene. Hydrogenation (Pd/C catalyst) of the tetrasubstituted olefin proceeded smoothly with acceptable stereoselectivity, depending on the diastereomer hydrogenated. The final compounds were then obtained in 12-18% overall yield through intramolecular cyclization, Jones oxidation, and hydrolysis in 5-7 steps from Garner's aldehyde.

引用

页码：44 / 47

页数：4

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