Huang Pei-Qiang, Wu Tian-Jun, Ruan Yuan-Ping
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005, P. R. China.
Org Lett. 2003 Nov 13;5(23):4341-4. doi: 10.1021/ol035617a.
[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.
[反应：见正文] 本文描述了一种合成5-烷基四嗪酸衍生物的灵活不对称方法，该方法基于使用9作为手性非外消旋四嗪酸5-碳负离子合成子9b的第一个合成等效物。通过用三甲基氯硅烷捕获，证明了碳负离子中间体9b的存在。本文还描述了本方法在抗真菌生物碱(+)-preussin以及受保护的(3S,4S)-AHPPA 6合成中的应用。
