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DOI: 10.1055/s-2000-8236
One-Step Oxidative Dimerization of Genuine, Unprotected Naphthylisoquinolines Alkaloids to Give Michellamines and Other Bioactive Quateraryls
Publication History
Publication Date:
31 December 2000 (online)
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The first one-step oxidative dimerization of monomeric naphthylisoquinoline alkaloids, using lead tetraacetate or phenyliodine(III) bis(trifluoroacetate) is described, thus avoiding previous 5- or 3-step reaction sequences involving protection, reduction, and deprotection reactions. The method is exemplified for the first nonenzymic direct preparation of michellamines A (1a) and C (1b) from korupensamines A (3a) and B (3b), respectively, and for the synthesis of the new quateraryl jozimine D (2), the unnatural dimer of natural dioncophylline B (5).
lead tetraacetate - phenyliodine(III) bis(trifluoroacetate) - michellamines - jozimine D - naphthylisoquinoline alkaloids - oxidative phenolic coupling - biaryls