A(1,3)-strain enabled retention of chirality during bis-cyclization of beta-ketoamides: total synthesis of (-)-salinosporamide A and (-)-homosalinosporamide A

作者：Nguyen Henry; Ma Gil; Romo Daniel^*

来源：Chemical Communications, 2010, 46(26): 4803-4805.

DOI：10.1039/c0cc00607f

A concise, enantioselective synthesis of the Phase I anticancer agent, (-)-salinosporamide A, is described. The brevity of the described strategy stems from a key bis-cyclization of a beta-keto tertiary amide, accomplished on gram scale, which retains optical purity enabled by A(1,3)-strain rendering epimerization slow relative to the rate of bis-cyclization. The versatility of the strategy for derivative synthesis is demonstrated by the synthesis of (-)-homosalinosporamide A.

• 出版日期2010