A short and efficient total synthesis of isoroquefortine C, the 3,12-(Z)-isomer of roquefortine C, from L-tryptophan methyl ester hydrochloride and 4(5)-(hydroxy)methylimidazole hydrochloride is described.
The copper-photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides( Ia nd Br) was reported. The reaction proceededu sing an ew heteroleptic Cu complex under irradiation with blue LEDs, givingt he corresponding boronic-acid esters in good to excellent yields. The reactionw as extended to continuous-flowc onditions to allow an easy scale-up. The mechanism of the reaction was studied and am echanism based on ar eductive quenching (Cu I /Cu I */Cu 0 )w as suggested.
The syntheses of isoroquefortine C and a related heterocycle were achieved by implementation of both intra-and intermolecular vinyl amidation reactions. These accomplishments represent a significant advance in the use of these strategies in the generation of complex molecules.
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