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Synlett 1994; 1994(4): 245-246
DOI: 10.1055/s-1994-22812
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New Synthesis of Phthalideisoquinoline Alkaloids via a Stereoselective Hydride Reduction of 1-(2′-Bromobenzoyl)-3,4-dihydroisoquinoline Methiodide, followed by Palladium-Catalyzed Carbonylation aided by Chlorotrimethylsilane

Kazuhiko Orito* , Mamoru Miyazawa, Hiroshi Suginome
  • *Organic Synthesis Division, Faculty of Engineering, Hokkaido University, Sapporo 060, Japan
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Publication Date:
22 March 2002 (online)

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A new method for the synthesis of phthalideisoquinoline alkaloids by the stereoselective reduction of 1-(2′-bromobenzoyl)-3,4-dihydroisoquinoline methiodide (4a) with sodium borohydride or lithium aluminium hydride, followed by a palladium-catalyzed carbonylation of the resultant erythro or threo alcohol (6a, 7) in the presence of chlorotrimethylsilane, is reported.