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A synthesis of the marine 4,6-dibromo-3-hydroxyoxoindoline convolutamydine C 3 is described. The key steps are the rhodium(II) perfluorobutyramide catalysed cyclisation of diazoamide 17 to give the oxoindoline 18, and the subsequent high yielding one-pot hydrolysis–decarboxylation–oxidation of 19 to 20. X-Ray crystal structures have been determined for the diazoamides 10 and 17 and for the oxoindolines 11 and 13.
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Miah et al. (1997) studied this question.
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