Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde
Diastereoselective Synthesis and Conformational Analysis of (2R)- and (2S)-Fluorostatines: An Approach Based on Organocatalytic Fluorination of a Chiral Aldehyde
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DOI：
10.1021/acs.orglett.5b03592
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发表时间：
2016-02-19
期刊：
影响因子：
5.2
通讯作者：
Hunter, Luke
中科院分区：
文献类型：
--
作者：
Hu, Xiang-Guo;Lawer, Aggie;Hunter, Luke
立体选择性氟化氨基酸他汀类似物已被有效合成。关键步骤是手性β -氧合醛的有机催化亲电氟化，这提供了非对映选择性和化学选择性的测试。发现目标他汀类药物类似物采用受氟间扭扭效应影响的独特构象，使其具有潜在的有价值的构建块，可纳入生物活性肽。
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.