Development of a practical synthesis of STA-5312, a novel indolizine oxalylamide microtubule inhibitor

…, Z Xia, S Chen, K Koya, M Ono, L Sun

Index: Li, Hao; Xia, Zhiqiang; Chen, Shoujun; Koya, Keizo; Ono, Mitsunori; Sun, Lijun Organic Process Research and Development, 2007 , vol. 11, # 2 p. 246 - 250

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Citation Number: 32

Abstract

An efficient synthesis of the novel microtubule inhibitor STA-5312 (3-[(4-cyanophenyl) methyl]-N-(3-methyl-5-isothiazolyl)-α-oxo-1-indolizineacetamide) was developed. A novel DMF/Me2SO4 directed regioselective synthesis of the 3-(4-cyanobenzoyl)-indolizine (4) was a critical transformation within the four-step process. Alternatively, a CuCl mediated synthesis of 3-(4-cyanobenzyl) indolizine (5) was also developed. All intermediates were ...