P-41 抗腫瘍活性物質Curacin Aの全合成(ポスター発表の部)

概要

論文の詳細を見る
Curacin A, which was isolated from cyanobacterium Lyngbya majuscula by Gerwick et al., has a potent inhibitory activity to the microtubule assembly. It shows selective cytotoxity for colon, renal, and breast cancer-derived cell lines. The characteristic feature of this compound consists of the thiazoline ring, cyclopropane unit, and long side chain contained four double bonds and one chiral center. We now describe here the total synthesis of curacin A. Our synthetic strategy for the construction of each chiral centers and double bonds are as follows: 1) The construction of C8-C17 fragment was achieved by employing the asymmetric allylation using allyldiisopinocamphenyl borane with the aldehyde, derived from geranyl acetate, under salt free condition. 2) C1-C7 fragment was derived from L-cysteine via salt free Wittig reaction. 3) Enantioselective synthesis of cyclopropane fragment (C18-C22) was accomplished by enzymatic approach using pig liver esterase. 4) C7-C8 E olefin was stereoselectively constructed by Julia coupling reaction. 5) Total synthesis of curacin A was achieved by the condensation of aminothiol derivative (C1-C17) with imino ether prepared in situ from cyclopropanecarboxamide.
天然有機化合物討論会の論文
1995-09-01