Azido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.

1 Introduction

2 Synthesis of α-Azido Acids

2.1 From α-Amino Acids or Esters

2.2 Via α-Substitution

2.3 Via Electrophilic Azidation

2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals

2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters

3 Synthesis of β-Azido Acids

3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids

3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine­ and AABA

4 Azido Acids in Total Synthesis

4.1 α-Azido Acids

4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain

5 Conclusions

叠氮酸是合成复杂肽的重要合成子。作为保护基，叠氮化物部分是原子有效的，易于安装并且可以在许多其他保护基存在下被还原，使其非常适合合成支链和/或环状肽。与氨基甲酸酯保护的对应物相比，α-叠氮基酸的体积较小，并且在难于形成的肽键和酯键的偶联反应中更有效地反应。叠氮酸还可用于在复杂的中间体上形成唑。这篇综述涵盖叠氮基酸的合成及其在复杂肽天然产物的总合成中的应用。

1引言

2α-叠氮酸的合成

2.1来自α-氨基酸或酯

2.2通过α替代

2.3通过亲电叠氮化

2.4通过N -2-叠氮基乙酰基-4-苯基噻唑烷二-2-噻吩烯醇与缩醛和缩醛的缩合

2.5α，β-不饱和α-叠氮酸和酯的合成

3β-叠氮酸的合成

3.1叠氮丙氨酸和3-叠氮基-2-氨基丁酸的制备

3.2除Azi doalanine和AABA以外的其他制备β-叠氮酸的一般方法

全合成中的4种叠氮酸

4.1α-叠氮基酸

4.2β-叠氮基酸和在侧链上含有叠氮基的叠氮基酸

5。结论