Asymmetric synthesis of (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives

被引：25

作者：

Koulocheri, SD

Magiatis, P

Skaltsounis, AL

Haroutounian, SA

机构：

[1] Agr Univ Athens, Chem Lab, Athens 11855, Greece

[2] Univ Athens, Dept Pharm, Athens 15771, Greece

来源：

TETRAHEDRON | 2002年 / 58卷 / 33期

关键词：

pipecolic acid; delta-lactam; 2-pyridone;

D O I：

10.1016/S0040-4020(02)00674-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical synthetic scheme that incorporates an amide functionality into the rigid framework of (2S,3R)-3-hydroxypipecolic acid to produce novel hydroxylated delta-lactam derivatives is reported. The reaction sequence includes the transformation of chiral furanylazide to a 2S-hydroxymethyldihydro pyridone, which was reduced diasteroselectively, protected and oxidized to two corresponding delta-lactam derivatives. Asymmetric dihydroxylation and oxidation of the latter compounds afforded two chiral (2R,3S)-3-hydroxypipecolic acid delta-lactam derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6665 / 6671

页数：7

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