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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
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Publication History

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

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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.

Key words

(S,R,R,R)-nebivolol - chiral pool - cyclization - synthesis design