A flexible approach to (S)-5-alkyl tetramic acid derivatives: application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA.
A flexible approach to (S)-5-alkyl tetramic acid derivatives: application to the asymmetric synthesis of (+)-preussin and protected (3S,4S)-AHPPA.
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DOI：
10.1021/ol035617a
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发表时间：
2003-10
期刊：
影响因子：
5.2
通讯作者：
Pei‐Qiang Huang;Tian-jun Wu;Yuanping Ruan
中科院分区：
文献类型：
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作者：
Pei‐Qiang Huang;Tian-jun Wu;Yuanping Ruan
[反应：描述了一种制备5-烷基特特拉姆酸衍生物的灵活的不对称方法，该方法基于使用9作为手性非外消旋特特拉姆酸5-碳负离子合成子9 b的第一个合成等价物。碳负离子中间体9 b的存在被三甲基氯硅烷捕获证实。本文还介绍了该方法在合成抗真菌生物碱（+）-普鲁辛和保护的（3S，4S）-AHPPA 6中的应用。
[reaction: see text] A flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with trimethylchlorosilane. Application of the present method to the synthesis of antifungal alkaloid (+)-preussin, as well as protected (3S,4S)-AHPPA 6, is also described.