Synthesis of a new enantiopure bicyclic γ/δ-amino acid (BTKa) derived from tartaric acid and α-amino acetophenone

被引：22

作者：

Guarna, A

Bucelli, I

Machetti, F

Menchi, G

Occhiato, EG

Scarpi, D

Trabocchi, A

机构：

[1] Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Florence, Italy

[2] CNR, Ist Chim Composti Organometallici, I-50019 Florence, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 49期

关键词：

amino acids and derivatives; amino ketones; peptide mimetics;

D O I：

10.1016/S0040-4020(02)01297-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a novel enantiopure gamma/delta-amino acid having the 3-aza-6,8-dioxabicyclo[3.2.1]octane structure was realized by the combination of tartaric acid derivatives and alpha-amino acetophenone followed by a trans-acetalisation process. This amino acid, which has a rigid skeleton and carries substituents at the 3, 5 and 7 positions of the scaffold, could find different applications in organic and peptidomimetic synthesis. Two different synthetic strategies were studied, one of them allowing the multigram scale preparation of the amino acid. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：9865 / 9870

页数：6

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