Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids.
Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids.
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使用衍生自市售 Fmoc α-氨基酸的杂环氨基酸对细环酰胺 A-D 进行固相合成和立体化学归属。
DOI：
10.1021/ol049020m
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发表时间：
2004
期刊：
影响因子：
--
通讯作者：
Kelly,JefferyW
中科院分区：
文献类型：
--
作者：
You,Shu-Li;Deechongkit,Songpon;Kelly,JefferyW
杂环氨基酸的固相组装使得能够全合成青年环酰胺AD的多种非对映异构体，建立或纠正每种天然产物的立体化学。该策略提供了一种非常有效的途径，可以从杂环氨基酸合成含噻唑和恶唑的大环内酰胺，而杂环氨基酸很容易由 Fmoc-α-氨基酸制备。该方法似乎广泛适用于出于药物发现目的而掺入非天然杂环氨基酸残基的天然产物库的合成。
The solid-phase assembly of heterocyclic amino acids enabled the total synthesis of numerous diastereoisomers of tenuecyclamides A−D, establishing or correcting the stereochemistry of each natural product. This strategy provides a very efficient route to synthesize thiazole- and oxazole-containing macrolactams from heterocyclic amino acids that are readily prepared from Fmoc-α-amino acids. This methodology appears to be broadly applicable to the synthesis of natural product libraries incorporating unnatural heterocyclic amino acid residues for the purpose of drug discovery.