A divergent approach to benzylisoquinoline-type and oxoaporphine alkaloids via regioselective direct ring metalation of alkoxy isoquinolines?
Organic & Biomolecular Chemistry Pub Date: 2015-06-09 DOI: 10.1039/C5OB00926J
Abstract
Methoxy- and benzyloxy-substituted isoquinolines are regioselectively metalated at C-1 with the Knochel–Hauser base, subsequent trapping with aromatic aldehydes gives aryl(isoquinolin-1-yl)carbinols as building blocks for divergent syntheses of different types of benzylisoquinoline alkaloids. Photochemical cyclization of ortho-bromo analogues under reductive conditions gives oxoaporphine alkaloids. Nine benzylisoquinoline alkaloids and two oxoaporphine alkaloids were obtained in two or three steps from appropriate isoquinolines.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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