98518-03-7Relevant academic research and scientific papers
Total Synthesis of Lycoricidine and Narciclasine by Chemical Dearomatization of Bromobenzene
Southgate, Emma H.,Holycross, Daniel R.,Sarlah, David
, p. 15049 - 15052 (2017)
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.
