Abstract
6-Iodoisocoumarin 4 and its aza-analogue, 6-iodo-1-oxo-isoquinoline 29, were efficiently prepared from vanillin in seven and six steps, respectively. Key
transformations in their syntheses were achieved by directed ortho-lithiation and variations of Horner-Wadsworth-Emmons reactions. Both 6-iodoisocoumarin
4 and its aza-analogue were designed for insertion into syntheses of rubromycin type
target structures via palladium-catalyzed coupling reactions. For the isocoumarin
subunit, this plan could be confirmed through Heck, Sonogashira, and Suzuki reactions
of our building block with various substrates.
Key words
isocoumarins - rubromycins -
ortho-lithiation - Horner-Wadsworth-Emmons reaction - palladium catalysis
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