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Synlett 1998; 1998(4): 387-388
DOI: 10.1055/s-1998-1666
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The Synthesis of 13-Spiro-substituted Protoberberines via the Tandem Addition - Cyclisation Reaction of 3-Methoxyphthalide Anions to 3,4-Dihydroisoquinolines

Ronald N. Warrener* , Ligong Liu, Richard A. Russell, Edward R. T. Tiekink
  • *Centre for Molecular Architecture, Central Queensland University, Rockhampton, Queensland, 4702, Australia; Fax + 61 749 30 99 17; E-mail: r.warrener@cqu.edu.au
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Publikationsdatum:
31. Dezember 2000 (online)

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The reaction of the anion of 3-methoxyphthalide with 3,4-dihydroisoquinolines affords 13-spiro-substituted protoberberines rather than the expected 8,13-dioxo derivatives. Whilst the parent 3,4-dihydroisoquinoline reacts stereospecifically to yield the (13S*,13aS*) diastereomer, the 1-methyl derivative affords exclusively the (13R*,13aS*) isomer. This change in stereochemical outcome is attributed to conformational changes induced by the methyl group in the putative 8,13-dioxo-intermediates.

anion addition - phthalides - 3,4-dihydroisoquinolines - protoberberines