Takahashi, Shunya Satoh, Daisuke Hayashi, Misato Takahashi, Kohta Yamaguchi, Kazunori Nakamura, Takemichi Koshino, Hiroyuki Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision This paper describes the first total synthesis of the proposed structure for aromin, an annonaceous acetogenin possessing an unusual bis-THF ring system, and its 4<i>S</i>,7<i>R</i>-isomer. The key steps involve an oxidative cyclization of a couple of terminal-diene alcohols and an intermolecular metathesis of an alkenyl tetrahydrofuran with an enone carrying a tetrahydrofuranyl lactone. The spectral data of both samples did not match those of aromin. Re-examination of the NMR data using the CAST/CNMR Structure Elucidator and chemical derivations suggested that the real structure of aromin should be revised to be a tetrahydropyran acetogenin, montanacin D. Cytotoxicities in human solid tumor cell lines for synthetic samples were also evaluated. terminal-diene alcohols;tetrahydrofuranyl lactone;oxidative cyclization;chemical derivations;NMR data;tumor cell lines;annonaceous acetogenin;tetrahydropyran acetogenin;sample;montanacin D;Total Synthesis;alkenyl tetrahydrofuran;bis-THF ring system;aromin;Structural Revision 2016-11-04
    https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_the_Proposed_Structure_for_Aromin_and_Its_Structural_Revision/4206657
10.1021/acs.joc.6b02187.s001