Eade, S. J., Walter, M. W., Byrne, C., Odell, B., Rodriguez, R., Baldwin, J. E., Adlington, R. M., Moses, J. E. (July 2008) Biomimetic synthesis of pyrone-derived natural products: exploring chemical pathways from a unique polyketide precursor. J Org Chem, 73 (13). pp. 4830-9. ISSN 0022-3263
Abstract
Our biomimetic hypothesis proposes that families of diverse natural products with complex core structures such as 9,10-deoxytridachione, photodeoxytridachione and ocellapyrone A are derived in nature from a linear and conformationally strained all-( E) tetraene-pyrone precursor. We therefore synthesized such a precursor and investigated its biomimetic transformation under a variety of reaction conditions, both to the above natural products as well as to diverse isomers which we propose to be natural products "yet to be discovered". We also report herein the first synthesis of the natural product iso-9,10-deoxytridachione.
| Item Type: | Paper |
|---|---|
| Additional Information: | The Journal of organic chemistry |
| Uncontrolled Keywords: | Biological Products/*chemical synthesis Macrolides/*chemistry Models, Molecular Molecular Structure Propionates/chemistry/metabolism Pyrones/*chemical synthesis |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 4 July 2008 |
| Date Deposited: | 19 Apr 2021 21:37 |
| Last Modified: | 19 Apr 2021 21:37 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/39533 |
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