New synthesis of (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate by configuration transform.
(R/S)-4,4'-Dimethoxy-5,6,5',6'-dimethenedioxy-2,2'-di-(4(S)-methyl-oxazoline-1)-biphenyl has been synthesized from dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate, and then the diastereoisomer mixture was almost fully converted to a single diastereoisomer with S-configuration ((S)-3) through the key configuration transform promoted by CuI, which was confirmed by CD, HPLC and (13)C NMR. The C(2)-symmetric biphenyl, (S)-dimethyl-4,4'-dimethoxy-5,6,5',6'-dimethenedioxy-biphenyl-2,2'-dicarboxylate was prepared easily via the hydrolysis and ester exchange of (S)-3.
Cheng
Sen-Xiang
SX
Center of Research, Henan Academy of Science, Zhengzhou, Henan 450002, China.
Chang
Jun-Biao
JB
Qu
Ling-Bo
LB
Chen
Rong-Feng
RF
D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D034242:Cyclooctanes / Q000138:chemical synthesis / Q000737:chemistry; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001713:Biphenyl Compounds; D034242:Cyclooctanes; D003998:Dicarboxylic Acids; D017705:Lignans; D011083:Polycyclic Compounds; C434677:dimethoxy biphenyl monocarboxylate; C031409:schizandrin C