Su Qibin, Beeler Aaron B, Lobkovsky Emil, Porco John A, Panek James S
Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Org Lett. 2003 Jun 12;5(12):2149-52. doi: 10.1021/ol034608z.
[reaction: see text] An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.
[反应:见正文] 描述了一种直接形成立体化学明确的大环二酯的快速方法。对映体富集的C7和C8羟基酯6在催化量的二锡氧烷酯交换催化剂存在下进行环二聚反应,得到含有多达六个立体中心的14至22元大环二酯7-9。通过对选定的大环二酯7a、7g、10a和11进行进一步的立体选择性反应,引入了额外的结构多样性。