Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde

被引：20

作者：

Hu, Xiang-Guo ^{[1
,2
]}

Lawer, Aggie ^{[2
]}

Peterson, Matthew B. ^{[2
,3
]}

Iranmanesh, Hasti ^{[2
]}

Ball, Graham E. ^{[2
]}

Hunter, Luke ^{[2
]}

机构：

[1] Jiangxi Normal Univ, Natl Engn Res Ctr Carbohydrate Synth, Nanchang 330022, Peoples R China

[2] UNSW Australia, Sch Chem, Sydney, NSW 2052, Australia

[3] Macquarie Univ, Dept Chem & Biomol Sci, Sydney, NSW 2109, Australia

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 04期

基金：

澳大利亚研究理事会;

关键词：

MICROBIAL AGENT AI-77-B; AMINO-ACIDS; ASYMMETRIC-SYNTHESIS; MEDICINAL CHEMISTRY; STEREOSELECTIVE-SYNTHESIS; PROTEASE INHIBITORS; ALPHA-FLUORINATION; PEPTIDES; ANALOGS; DERIVATIVES;

D O I：

10.1021/acs.orglett.5b03592

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselctively fluorinated analogues of the amino acid statine have been efficiently synthesized. The key step is an organocatalytic electrophilic fluorination of a chiral beta-oxygenated aldehyde, which provided a test of both diastereoselectivity and chemoselectivity. The target statine analogues were found to adopt unique conformations influenced by the fluorine gauche effect, rendering them potentially valuable building blocks for incorporation into bioactive peptides.

引用

页码：662 / 665

页数：4

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