Tetrahedron

Syntheses of (S)-(−)-pindolol and [3′-13 C]-(R)-(−)-pindolol utilizing a lanthanum-lithium-(R)-BINOL ((R)-LLB) catalyzed nitroaldol reaction

H Sasai, YMA Yamada, T Suzuki, M Shibasaki

Index: Sasai, Hiroaki; Yamada, Yoichi M. A.; Suzuki, Takeyuki; Shibasaki, Masakatsu Tetrahedron, 1994 , vol. 50, # 43 p. 12313 - 12318

Full Text: HTML

Citation Number: 65

Abstract

An efficient synthesis of (−)-pindolol, an effective β-blocker, has been achieved utilizing a lanthanum-lithium-(R)-BINOL ((R)-LLB) catalyzed nitroaldol reaction as a key step. This methodology was applicable to a synthesis of 13C-labeled (−)-pindolol, which would be useful as a biological tool for tracing the metabolism of β-blocker and 5-HT1A receptor antagonist. The mechanistic aspects of the LLB catalyzed nitroaldol reaction are also ...