Dickson David P, Wardrop Duncan J
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
Org Lett. 2009 Mar 19;11(6):1341-4. doi: 10.1021/ol900133v.
A stereoselective synthesis of agelastatin A, a potent cytotoxin and inhibitor of osteopontin (OPN)-mediated neoplastic transformations, has been accomplished in 14 steps (12 operations) with an approximate overall yield of 8%. Notable features of this route include the direct manner in which the pyrroloketopiperazine A-ring of the target is generated and the efficient employment of a trichloroacetamide, introduced through Overman rearrangement, as a protecting group, pendant nucleophile, and latent urea.
已通过14步反应（12步操作）完成了对agelastatin A的立体选择性合成，agelastatin A是一种强效细胞毒素，也是骨桥蛋白（OPN）介导的肿瘤转化的抑制剂，总产率约为8%。该路线的显著特点包括直接生成目标化合物吡咯并酮哌嗪A环的方式，以及通过奥弗曼重排引入的三氯乙酰胺作为保护基、侧链亲核试剂和潜在尿素的有效应用。
