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Aporphine Alkaloid Synthesis and Diversification via Direct Arylation
Author(s) -
Lafrance Marc,
Blaquiere Nicole,
Fagnou Keith
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600674
Subject(s) - chemistry , enantioselective synthesis , aporphine , pyrazine , catalysis , pyridine , organic chemistry , palladium , yield (engineering) , alkaloid , combinatorial chemistry , stereochemistry , materials science , metallurgy
Palladium‐catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2‐substituted aporphines by reaction with benzodioxole, pyridine N ‐oxide and pyrazine N ‐oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of ( R )‐nornuciferine and ( R )‐nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)