Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene.

ABSTRACT: The total synthesis of lycoricidine and narciclasine is enabled by an arenophile-mediated dearomative dihydroxylation of bromobenzene. Subsequent transpositive Suzuki coupling and cycloreversion deliver a key biaryl dihydrodiol intermediate, which is rapidly converted into lycoricidine through site-selective syn-1,4-hydroxyamination and deprotection. The total synthesis of narciclasine is accomplished by the late-stage, amide-directed C-H hydroxylation of a lycoricidine intermediate. Moreover, the general applicability of this strategy to access dihydroxylated biphenyls is demonstrated with several examples.

SUBMITTER: Southgate EH 

PROVIDER: S-EPMC5971115 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature