Synthesis 2007(8): 1154-1158  
DOI: 10.1055/s-2007-965993
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (S,R,R,R)-α,α′-Iminobis(methylene)bis(6-fluoro-3H,4H-dihydro-2H-1-benzopyran-2-methanol)

Nai-Xing Wang*a, An-Guang Yua, Gui-Xia Wanga, Xiu-Hui Zhangb, Qian-Shu Lib, Zhen Lib
a Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. of China
Fax: +86(10)62554670; e-Mail: nxwang@mail.ipc.ac.cn;
b Insititute of Beijing Technology, Beijing 100081, P. R. of China
Further Information

Publication History

Received 12 October 2006
Publication Date:
23 March 2007 (online)

Abstract

The β1-adrenergic antagonist (S,R,R,R)-α,α′-iminobis(methylene)bis(6-fluoro-3H,4H-dihydro-2H-1-benzopyran-2-methanol) was synthesized from natural chiral pool starting materials through an efficient, convergent synthetic strategy. The cyclization mechanism of the key step was investigated using computer modeling and is discussed.

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