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Synthesis, Separation, and Theoretical Studies of Chiral Biphenyl Lignans (α- and β-DDB)

✍ Scribed by Junbiao Chang; Rongfeng Chen; Ruiyun Guo; Chunhong Dong; Kang Zhao

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
120 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Two biphenyl lignans, α‐ and β‐DDB (1 and 2, respectively) were efficiently synthesized without contamination by other regio‐isomers. The different yields of the Ullmann coupling reactions for the synthesis of 1 and 2 were rationalized by calculating steric hindrance, stability, entropy change, and heat‐of‐formation values. The enantiomers of 1 and 2 were readily separated by HPLC on a chiral stationary phase. Their configurations were assigned based on the Cotton effect of the authentic natural products.

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