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Biomimetic Total Synthesis of (±)-Doitunggarcinone A and (+)-Garcibracteatone

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journal contribution
posted on 21.03.2014, 00:00 by Henry P. Pepper, Stephen J. Tulip, Yuji Nakano, Jonathan H. George
A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.