Synthesis of Pseudodeflectusin and Ustusorane C: Structural Revision of Aspergione A and B

Kouji KURAMOCHI; Fumiyo SAITO; Atsuo NAKAZAKI; Toshifumi TAKEUCHI; Kazunori TSUBAKI; Fumio SUGAWARA; Susumu KOBAYASHI

doi:10.1271/bbb.100241

Organic Chemistry Regular Papers

Synthesis of Pseudodeflectusin and Ustusorane C: Structural Revision of Aspergione A and B

Kouji KURAMOCHI, Fumiyo SAITO, Atsuo NAKAZAKI, Toshifumi TAKEUCHI, Kazunori TSUBAKI, Fumio SUGAWARA, Susumu KOBAYASHI

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Keywords: total synthesis, natural product, aromatic compound, carbonyl compound, stereochemistry

JOURNAL FREE ACCESS

2010 Volume 74 Issue 8 Pages 1635-1640

DOI https://doi.org/10.1271/bbb.100241

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Abstract

The syntheses of racemic and optically active pseudodeflectusin and ustusorane C are described. The ¹H- and ¹³C-NMR data for our synthetic pseudodeflectusin and ustusorane C were identical to those of the corresponding natural products. We also synthesized the proposed structure of aspergione A and B whose ¹H- and ¹³C-NMR data were identical to those of ustusorane C and pseudodeflectusin. The ¹H- and ¹³C-NMR spectra of our synthetic aspergione A and B were different from those of the natural compounds. Our results confirm that aspergione A and B are in fact ustusorane C and pseudodeflectusin, respectively.

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