Synthesis and Absolute Configuration of (+)-Pseudodeflectusin: Structural Revision of Aspergione B

We report herein the total synthesis and determination of the absolute configuration of (+)‐pseudodeflectusin. The total synthesis of (+)‐pseudodeflectusin starting from o‐anisic aid was achieved in 11 total steps with an overall yield of 2.0 %. The 1H‐ and 13C NMR spectroscopic data of our synthetic pseudodeflectusin was identical to that of the natural compound. The absolute configuration of (+)‐pseudodeflectusin was determined by chiral HPLC and X‐ray crystallographic analyses. We also synthesized the proposed structure of aspergione B, whose 1H‐ and 13C NMR spectroscopic data is identical to that of pseudodeflectusin. The 1H‐ and 13C NMR spectra of our synthetic aspergione B were different from those of the natural compound reported by Proksch et al. Our results confirm that aspergione B and pseudodeflectusin are, in fact, the same compound.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)