Tetrahedron

Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine

J Ni, H Xiao, L Weng, X Wei, Y Xu

Index: Ni, Jizhi; Xiao, Heping; Weng, Lipeng; Wei, Xiaofeng; Xu, Youjun Tetrahedron, 2011 , vol. 67, # 29 p. 5162 - 5167

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Citation Number: 7

Abstract

Abstract A new approach for the diastereoselective synthesis of (±)-α-noscapine, a phthalide tetrahydroisoquinoline alkaloid exhibiting several biological activities, is described. The strategy features a blocking group-directed Bischler–Napieralski reaction followed by diastereoselective reduction (α/β> 23: 1). One of the key intermediates, phthalide-3- carboxylic acid, could be efficiently prepared from simple benzoic acid derivative and ...