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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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Communication
Total Synthesis of (±)-Trichodermamide B and of a Putative Biosynthetic Precursor to Aspergillazine A Using an Oxaza-Cope Rearrangement†
Article first published online: 24 JUL 2008
DOI: 10.1002/anie.200801652
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lu, C.-D. and Zakarian, A. (2008), Total Synthesis of (±)-Trichodermamide B and of a Putative Biosynthetic Precursor to Aspergillazine A Using an Oxaza-Cope Rearrangement. Angew. Chem. Int. Ed., 47: 6829–6831. doi: 10.1002/anie.200801652
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Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 24 JUL 2008
- Manuscript Received: 8 APR 2008
Funded by
- Department of Chemistry and Biochemistry, Florida State University
- ACS Petroleum Research Fund. Grant Number: 43838-G1
- NSF. Grant Number: CAREER CHE-0746881
- MDS Research Foundation
Keywords:
- heterocycles;
- natural products;
- peptides;
- sigmatropic rearrangement;
- total synthesis
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.