Robichaud Joël, Tremblay François
Merck Frosst Canada Ltd., 16711 Trans Canada Highway, Kirkland, Québec H9H 3L1, Canada.
Org Lett. 2006 Feb 16;8(4):597-600. doi: 10.1021/ol0527328.
[reaction: see text] The challenging structural features and important biological activity of (+)-compactin (1) explain the substantial synthetic interest that it has generated. We report a novel enantioselective approach to the advanced intermediate 2a, which constitutes a formal synthesis of (+)-1. The sequence utilizes MacMillan's organocatalytic Mukaiyama-Michael reaction, which stereoselectively adds the silyloxyfuran 6 to alpha,beta-unsaturated aldehyde 7. The chirality generated in this reaction guides the formation of the other three consecutive stereocenters found in 2a.
[反应：见正文]（+）-康帕丁（1）具有挑战性的结构特征和重要的生物活性解释了它所引发的大量合成研究兴趣。我们报道了一种合成高级中间体2a的新型对映选择性方法，该方法构成了（+）-1的形式合成。该反应序列利用了麦克米伦的有机催化 Mukaiyama-Michael反应，该反应将甲硅烷氧基呋喃6立体选择性地加成到α，β-不饱和醛7上。此反应中产生的手性引导了在2a中发现的其他三个连续立体中心的形成。
