Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336, United States.
J Org Chem. 2011 Oct 7;76(19):8027-32. doi: 10.1021/jo201210u. Epub 2011 Sep 1.
The formal synthesis of the marine natural product (-)-cyanolide A is presented. The synthetic strategy is centered on two acyclic diastereoselective reactions and a single cyclic reaction with modest to excellent dr based on an initial stereocenter. Most notable is a highly stereoselective oxocarbenium reduction based on a "mismatched" reactive conformer to afford the β-C-glycoside subunit leading to an efficient synthesis of the diolide aglycon in 12 overall steps.
本文呈现了海洋天然产物（-）-氰醇 A 的全合成。该合成策略以两个非环的立体选择性反应和一个基于初始立体中心的单环反应为中心，基于适度至优异的 dr 值。最值得注意的是一种高度立体选择性的氧杂卡宾还原，基于一个“不匹配”的反应构象，以提供β-C-糖苷亚基，从而在 12 步总步骤中高效合成二醇内酯的苷元。
