A new route which is germane to the synthesis of 9,10-oxygenated tetrahydroprotoberberines and 8-oxoprotoberberines is described. The route features the use of a diester () generated from reaction of dimethylmalonate with an aryl halide in the presence of -butyllithium. The amide prepared in subsequent steps is a versatile precursor for the synthesis of tetrahydroprotoberberine and 8-oxoprotoberberine scaffolds using standard high-yielding reactions. In this manner, (±)-isocorypalmine and oxypalmatine have been synthesized in 23% and 22 % yields respectively.
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| http://dx.doi.org/10.1016/j.tet.2015.01.004 | DOI Listing |
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A divergent route to 9, 10-oxygenated tetrahydroprotoberberine and 8-oxoprotoberberine alkaloids: synthesis of (±)-isocorypalmine and oxypalmatine.
Tetrahedron
February 2015
Hunter College, City University of New York, 695 Park Avenue, NY 10065, USA ; The Graduate Center, City University of New York, 365 5th Avenue, NY 10016, USA.
A new route which is germane to the synthesis of 9,10-oxygenated tetrahydroprotoberberines and 8-oxoprotoberberines is described. The route features the use of a diester () generated from reaction of dimethylmalonate with an aryl halide in the presence of -butyllithium. The amide prepared in subsequent steps is a versatile precursor for the synthesis of tetrahydroprotoberberine and 8-oxoprotoberberine scaffolds using standard high-yielding reactions.
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J Pharm Biomed Anal
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Department of International Development Engineering, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan.
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