- Synthesis of (+)-O-methylthalibrine by employing a stereocontrolled Bischler-Napieralski reaction and an electrochemically generated diaryl ether
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An efficient electrochemical four-step route was developed for the preparation of diaryl ether derivatives by using halogenation and dehalogenation processes in addition to electrochemical phenolic oxidation and reduction reactions. The synthesis of (+)-O
- Kawabata, Yuki,Naito, Yu,Saitoh, Tsuyoshi,Kawa, Kohei,Fuchigami, Toshio,Nishiyama, Shigeru
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- Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile
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Under controlled conditions, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline- 1-carbonitrile can be quantitatively deprotonated in the α-position. Its alkylation directly furnishes 3,4-dihydroisoquinolines which can serve as starting materials for the preparation of various alkaloids. Here, the preparation of the benzylisoquinolines (+)-laudanidine, (+)-armepavine, and (+)-laudanosine as well as the tetrahydroprotoberberines ( - )-corytenchine and ( - )-tetrahydropseudoepiberberine using Noyori's asymmetric transfer hydrogenation are described. The dimeric alkaloids (+)-O-methylthalibrine and (+)-tetramethylmagnolamine were obtained from nonracemic precursors in Ullmann diaryl ether syntheses.
- Blank, Nancy,Opatz, Till
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p. 9777 - 9784
(2012/01/30)
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