Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition

作者：Davies Stephen G^*; Ichihara Osamu; Roberts Paul M; Thomson James E

来源：Tetrahedron, 2011, 67(1): 216-227.

DOI：10.1016/j.tet.2010.10.067

• Asymmetric synthesis
• Lithium amide
• (+)-Negamycin
• (+)-3-epi-Negamycin
• Sperabillin C

The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(alpha-methylbenzyl)amide to an alpha,beta-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials.

• 出版日期2011-1-7