用于非对映选择性合成4E-烯基顺式-1,3-二醇的串联共轭加成-消除反应

Tandem conjugate addition-elimination for the diastereoselective synthesis of 4E-alkenyl syn-1,3-diols.

作者信息

Rotulo-Sims Delphine, Prunet Joëlle

机构信息

Laboratoire de Synthèse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.

出版信息

Org Lett. 2007 Oct 11;9(21):4147-50. doi: 10.1021/ol701624y. Epub 2007 Sep 19.

DOI:10.1021/ol701624y

PMID:17880094

Abstract

We have developed a tandem conjugate addition-elimination sequence for the diastereoselective synthesis of protected allylic syn-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21-C25 fragment of Dolabelide C.

摘要

我们已经开发出一种串联共轭加成-消除序列，用于从乙烯基砜开始非对映选择性合成受保护的烯丙基顺式-1,3-二醇。然后用钠汞齐还原磺酰基，以提供E-烯烃作为主要异构体。该方法被应用于合成模拟多拉贝利德C的C21-C25片段的三取代烯烃。