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One-Pot Enantiomeric Synthesis of Thiazole-Containing Amino Acids: Total Synthesis of Venturamides A and B
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acs.joc.8b00244
Yi Liu 1, 2 , Peng He 1, 3 , Yang Zhang 1, 3 , Xiangyu Zhang 2 , Jun Liu 1 , Yuguo Du 1, 3
Affiliation  

An effective one-pot procedure for enantiomerical synthesis of thiazole-containing amino acid (TCAA) has been established via a cascade disulfide cleavage/thiocarbonylation/intramolecular Staudinger reduction/aza-Wittig/oxidation reaction. Starting from the commercially available amino acid building blocks, a number of TCAAs were prepared in good yields and with excellent optical purities. This method bears features of mild reaction conditions, wide substrate adaptability, and good functional group tolerance. The power of this method was also demonstrated through the concise total synthesis of cyclic hexapeptide Venturamides A and B.

中文翻译:

含噻唑的氨基酸的一锅对映体合成:文图酰胺A和B的全合成

通过级联二硫键裂解/硫代羰基化/分子内斯托丁格还原/氮杂-维蒂希/氧化反应,已经建立了一种有效的一锅法,用于对映体合成含噻唑的氨基酸(TCAA)。从可商购的氨基酸构件开始,以高收率和优异的光学纯度制备了许多TCAA。该方法具有反应条件温和,底物适应性广,官能团耐受性好的特点。环状六肽Venturamides A和B的简明全合成也证明了该方法的强大功能。
更新日期:2018-03-13
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