Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J
Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J
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DOI：
10.1021/acs.orglett.5b01848
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发表时间：
2015-08-07
期刊：
影响因子：
5.2
通讯作者：
Willis, Christine L.
中科院分区：
文献类型：
--
作者：
Ackrill, Thomas D.;Sparkes, Hazel A.;Willis, Christine L.
以邻羟基肉桂醛为原料，经过两步反应可有效地制备伽马、三角洲不饱和醇类化合物。TMSOTf介导的伽马，三角洲-不饱和醇与醛的反应在一个锅中产生了两个氧杂环和三个新的立体中心。这种方法是多才多艺的，通过改变硼酸、格氏试剂和醛，可以引入不同的取代基，而在共轭加成中使用手性碱可以得到富含对映体的产物。
gamma,delta-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the gamma,delta-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.