TY - DATA T1 - Biomimetic Total Synthesis of (±)-Doitunggarcinone A and (+)-Garcibracteatone PY - 2014/03/21 AU - Henry P. Pepper AU - Stephen J. Tulip AU - Yuji Nakano AU - Jonathan H. George UR - https://acs.figshare.com/articles/journal_contribution/Biomimetic_Total_Synthesis_of_Doitunggarcinone_A_and_Garcibracteatone/2312809 DO - 10.1021/jo500027k.s004 L4 - https://ndownloader.figshare.com/files/3950443 KW - garcibracteatone KW - monoterpene fragments KW - target molecules KW - cyclization approach KW - Novel syntheses KW - enantioselective synthesis KW - doitunggarcinone KW - configuration N2 - 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. ER -