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Total syntheses of kealiinines A-C.

ABSTRACT: Short total syntheses of the Leucetta-derived alkaloids, kealiinines A-C, have been accomplished using an intramolecular Friedel-Crafts-dehydration sequence of a bis benzylic diol. The precursor diol was obtained through a series of position-specific Grignard reactions from 1-methyl-4,5-diiodoimidazole. C2-Azidation and hydrogenation of the azide then provided the reported structures of kealiinines A-C. While the (1)H NMR data did not completely match for these materials, the HPLC data were consistent with the assigned structure of these alkaloids.

SUBMITTER: Das J

PROVIDER: S-EPMC3876472 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Total syntheses of kealiinines A-C.

Das Jayanta J Koswatta Panduka B PB Jones J Daniel JD Yousufuddin Muhammed M Lovely Carl J CJ

Organic letters 20121205 24

Short total syntheses of the Leucetta-derived alkaloids, kealiinines A-C, have been accomplished using an intramolecular Friedel-Crafts-dehydration sequence of a bis benzylic diol. The precursor diol was obtained through a series of position-specific Grignard reactions from 1-methyl-4,5-diiodoimidazole. C2-Azidation and hydrogenation of the azide then provided the reported structures of kealiinines A-C. While the (1)H NMR data did not completely match for these materials, the HPLC data were cons ...[more]

PMID: 23215346

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