Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile

N Blank, T Opatz

Index: Blank, Nancy; Opatz, Till Journal of Organic Chemistry, 2011 , vol. 76, # 23 p. 9777 - 9784

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Citation Number: 13

Abstract

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 (−)- ...