Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Total Synthesis of Lycoricidine and Narciclasine via Chemical Dearomatization of Bromobenzene

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

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709712

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