Total Synthesis of (±)-Trichodermamide B and of a Putative Biosynthetic Precursor to Aspergillazine A Using an Oxaza-Cope Rearrangement


  • This work was supported by the Department of Chemistry and Biochemistry, Florida State University, the ACS Petroleum Research Fund (43838-G1), and NSF (CAREER CHE-0746881). C.-D.L. thanks the MDS Research Foundation for a postdoctoral fellowship. We thank Dr. U. Goli (FSU) for assistance with HRMS experiments. We thank Dr. Capon for a copy of the 1H NMR spectrum of aspergillazine A.


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Coping with tandem reactions: The total synthesis of marine fungal metabolite, trichodermamide B, is accomplished using a tandem nitrosation/oxaza-Cope rearrangement as the key step to establish the characteristic heterocyclic ring system of the natural product. Preparation of the putative biosynthetic precursor of aspergillazine A provides further insight into the possible biosynthetic pathway to aspergillazines.