Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A
Iterative oxazole assembly via α-chloroglycinates:: Total synthesis of (-)-muscoride A
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DOI：
10.1002/anie.200390363
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发表时间：
2003-01-01
影响因子：
16.6
通讯作者：
Ciufolini, MA
中科院分区：
文献类型：
--
作者：
Coqueron, PY;Didier, C;Ciufolini, MA
正在进行的针对含恶唑天然产物合成的工作揭示了基于方案 1 所示方法的温和迭代恶唑构建方法的需求。 [1]通用的伯酰胺 1（可能衍生自 α-氨基酸）将被改进为恶唑-4-甲酰胺 2，经过相同的反应序列后会生成双恶唑 3。经过 n 次这样的迭代后，将形成带有不同取代基 R 的聚恶唑 4。记录的简单 N-酰基炔丙胺的环化（例如 5a！6a，方案 2）[2] 提供了一种有吸引力的方法。 解决了恶唑组装的问题，前提是转化可以用炔基甘氨酸型底物 5b 实现，其中 R1 可能含有潜在不稳定的立体中心。此外，这种逻辑要求内部
Ongoing work directed toward the synthesis of oxazolecontaining natural products revealed the desirability for a mild method for iterative oxazole construction based on the approach shown in Scheme 1.[1] A generic primary amide 1 (possibly derived from an α-amino acid) would be advanced to oxazole-4-carboxamide 2, which upon subjection to the same reaction sequence leads to bisoxazole 3. A polyoxazole 4 bearing diverse substituents R would materialize after n such iterations.The documented cyclization of simple N-acyl propargylamines (eg 5a! 6a, Scheme 2)[2] offered an attractive solution to the issue of oxazole assembly, provided that the transformation could be effected with alkynylglycine-type substrates 5b, in which R1 may contain potentially labile stereocenters. Furthermore, this logic requires that inter-