Synthetic investigations of isoquinoline alkaloids.

  • E. P. Tiley

Student thesis: Doctoral ThesisPhD


Several synthetic routes towards 3-aryl-7,8-dimethoxyisoquinolines were investigated to provide intermediates for berbines and benzo-[c]-phenanthridines. A facile synthesis of 3-aryl-7,8-dioxygenated isocoumarins was obtained by conversions to isoquinoline derivatives were unsuccessful. A novel route to an benzylaminophenyl-acetaldehyde dimethyl acetal was accomplished, with subsequent ring closure to a 3-siryl-7,8-dimethoxyisoquinoline. The preparation of dissymmetrically substituted desoxy-benzoins was briefly investigated and, through the intermediate conversion of a desoxybenzoin to a 3-aryl-8-hydroxy-7-methoxy-isoquinoline, the alkaloid Berberastine was synthesized.
Date of Award1973
Original languageEnglish
Awarding Institution
  • University of Bath

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