Total syntheses of (-)-hanishin, (-)-longamide B, and (-)-longamide B methyl ester via a novel preparation of N-substituted pyrrole-2-carboxylates [corrected].
A novel preparation of N-substituted pyrrole-2-carboxylates has been developed based upon 1,3-dipolar cycloaddition and a conventional hydrogenolysis. By using this method as the key step, total syntheses of natural alkaloids (-)-hanishin, (-)-longamide [corrected] B, and (-)-longamide [corrected] B methyl ester were accomplished in the highest overall yields, respectively.
Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China.
Guolin
G
Cheng
Xinyan
X
Wang
Hailin
H
Bao
Chuanjie
C
Cheng
Nan
N
Liu
Yuefei
Y
Hu
D004952:Esters / Q000737:chemistry*; D006865:Hydrogenation; D008745:Methylation; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D004952:Esters; D011758:Pyrroles; C511000:hanishin; C572041:longmide B; C002986:2-pyrrolecarboxylic acid; D011392:Proline