Palladium catalyzed insertion of carbon monoxide into benzyl-tetrahydroisoquinolines : A new synthesis of berbine alkaloids |
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Authors: | Ganesh D Pandey Kamala P Tiwari |
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Institution: | Department of Chemistry, University of Allahabad, Allahabad-211 002, India |
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Abstract: | A new total synthesis of the berbine alkaloid ring system has been achieved. Palladium catalyzed insertion of carbon monoxide into the 1 - (2 - bromobenzyl) - substituted - 1,2,3,4 - tetrahydroisoquinolines (1a–1d) by the use of catalytic amounts of palladium diacetate and triphenylphosphine in the presence of tri-n-butylamine afforded the berbin-8-ones (2a–2d) which, on reduction with lithium aluminium hydride gave the berbines (±)-berbine 3a, (±)2,3-dimethoxyberbine 3b, (±)-xylopinine 3c and (±)-pseudoepitetrahydroberbine 3d. |
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Keywords: | Present address-Hygiejnisk Institut J B Winsløwsvej 19 D K 5000 Odense Universitet Odense C Denmark |
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