jo6b02187_si_002.pdf (3.94 MB)
Total Synthesis of the Proposed Structure for Aromin and Its Structural Revision
journal contribution
posted on 2016-11-04, 13:30 authored by Shunya Takahashi, Daisuke Satoh, Misato Hayashi, Kohta Takahashi, Kazunori Yamaguchi, Takemichi Nakamura, Hiroyuki KoshinoThis
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.