Total synthesis of (+)-zaragozic acid C
Total synthesis of (+)-zaragozic acid C
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DOI：
10.1021/jo000700m
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发表时间：
2000-10-20
影响因子：
3.6
通讯作者：
Ahmed, G
中科院分区：
文献类型：
--
作者：
Armstrong, A;Barsanti, PA;Ahmed, G
报道了（+）-萨拉戈萨酸C的全合成方法。合成的关键特征是使用二烯6的双重Sharpless不对称二羟基化反应以控制C3至C6的四个相邻立构中心处的立体化学;通过衍生自二噻烷单亚砜27的阴离子与核心醛12之间的反应引入C1-侧链;高产率、酸介导的同时丙酮化合物脱保护-二噻烷去除-缩酮化程序，其仅导致2，8-二氧杂双环[3.2.1]辛烷核34;以及一种新的三重氧化方法，其允许安装三羧酸。
A total synthesis of (+)-zaragozic acid C is described. Key features of the synthesis are the use of a double Sharpless asymmetric dihydroxylation reaction of diene 6 to control stereochemistry at four contiguous stereocenters from C3 to C6; the introduction of the C1-side chain by reaction between the anion derived from the dithiane monosulfoxide 27 and the core aldehyde 12; a high yielding, acid-mediated simultaneous acetonide deprotection-dithiane removal-ketalization procedure leading exclusively to the 2,8-dioxabicyclo[3.2.1]octane core 34; and a novel triple oxidation procedure allowing installation of the tricarboxylic acid.