Synthesis of defucogilvocarcin V isosteres via MAD-mediated conjugate addition of carbanions to naphthoquinone ketals

Article abstract of DOI:10.1016/S0040-4020(96)00054-3

Treatment of a complex between naphthoquinone ketal 7 and methylaluminum bis(2,6-di-tert-butyl-4-methylphenoxide (MAD) with aryllithium reagents prepared by metallation of oxazoline 13 and amide 18, gave conjugate adducts which were converted to defucogilvocarcin V analogs 2 and 3 via a short reaction sequence. Some problems encountered in the metallation of oxazoline 19, a structural analog of amide 18, are also described.