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. Author manuscript; available in PMC: 2012 May 9.
Published in final edited form as: ACS Comb Sci. 2011 Mar 25;13(3):232–243. doi: 10.1021/co100054e

Scheme 2.

Scheme 2

Hydrogen peroxide treatment oxidizes the phenyl boronic acid to the phenol and subsequent treatment with CNBr under acidic conditions cleaves the methyl phenol moiety from SLs altogether. It is suggested that this moiety is oxidized to the quinine methide.