Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision
2016
Takahashi, Shunya | Satoh, Daisuke | Hayashi, Misato | Takahashi, Kohta | Yamaguchi, Kazunori | Nakamura, Takemichi | Koshino, Hiroyuki
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 4S,7R-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.
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