Studies directed toward the total synthesis of azaspiracid:: Stereoselective construction of C1-C12, C13-C19, and C21-C25 fragments
Studies directed toward the total synthesis of azaspiracid:: Stereoselective construction of C1-C12, C13-C19, and C21-C25 fragments
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DOI：
10.1021/ol006674w
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发表时间：
2000-11-30
期刊：
影响因子：
5.2
通讯作者：
Weldon, DJ
中科院分区：
文献类型：
--
作者：
Carter, RG;Weldon, DJ
概述了阿司匹酸的C-1-C-12、C-13-C-19和C-21-C-25片段的有效进入。C-1-C-12部分是用关键的不对称烯基硼烷与相应的α，β-不饱和醛加成而成的。C-13-C-19部分的合成采用了Evans不对称烷基化反应，然后是夏普莱斯不对称双羟基化反应。此外，还详细介绍了一种解决相邻手性恶唑烷酮在夏普莱斯双羟基化反应中失配效应的新方法。
The efficient entry to the C-1-C-12, C-13-C-19, and C-21-C-25 fragments of azaspiracid is outlined. The C-1-C-12 portion is constructed using a key asymmetric allenyl borane addition to the corresponding alpha,beta -unsaturated aldehyde. The synthesis of the C-13-C-19 portion utilizes an Evans asymmetric alkylation followed by Sharpless asymmetric dihydroxylation. In addition, a novel solution to the mismatched effects of a neighboring chiral oxazolidinone during a Sharpless dihydroxylation is detailed.