Rodriguez, R., Adlington, R. M., Eade, S. J., Walter, M. W., Baldwin, J. E., Moses, J. E. (May 2007) Total synthesis of cyercene A and the biomimetic synthesis of (+/-)-9,10-deoxytridachione and (+/-)-ocellapyrone A. Tetrahedron, 63 (21). pp. 4500-4509. ISSN 0040-4020
Abstract
This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.
| Item Type: | Paper |
|---|---|
| Additional Information: | Tetrahedron |
| Uncontrolled Keywords: | total synthesis natural products electrocyclisation reaction cascade methide intermediate generation streptomyces-spectabilis polypropionate pyrones efficient method marine mollusks metabolites snf4435c biosynthesis propionate spectinabilin Chemistry |
| CSHL Authors: | |
| Depositing User: | Matthew Dunn |
| Date: | 21 May 2007 |
| Date Deposited: | 17 Nov 2020 21:32 |
| Last Modified: | 17 Nov 2020 21:32 |
| URI: | https://repository.cshl.edu/id/eprint/39794 |
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