Rodriguez, R., Moses, J. E., Adlington, R. M., Baldwin, J. E. (October 2005) A new and efficient method for o-quinone methide intermediate generation: application to the biomimetic synthesis of the benzopyran derived natural products (+/-)-lucidene and (+/-)-alboatrin. Org Biomol Chem, 3 (19). pp. 3488-95. ISSN 1477-0520 (Print)1477-0520
Abstract
Lucidene and alboatrin are complex benzopyran derived natural products. A key step in their biogenesis may involve a hetero Diels-Alder cycloaddition between an o-quinone methide intermediate with a simple, or activated tri-substituted olefin. Experimental evidence is provided to support this hypothesis, with the biomimetic synthesis of both (+/-)-lucidene and (+/-)-alboatrin successfully achieved using a new and efficient method for o-quinone methide generation.
| Item Type: | Paper |
|---|---|
| Additional Information: | Organic & biomolecular chemistry |
| Uncontrolled Keywords: | Alkenes/chemistry Benzopyrans/*chemistry Benzoquinones/*chemical synthesis Biological Products/*chemical synthesis Biomimetics Cyclization Indolequinones/*chemistry Models, Chemical Quinones/*chemical synthesis Sesquiterpenes/*chemical synthesis |
| CSHL Authors: | |
| Communities: | CSHL labs > Moses lab |
| Depositing User: | Matthew Dunn |
| Date: | 7 October 2005 |
| Date Deposited: | 19 Apr 2021 21:30 |
| Last Modified: | 19 Apr 2021 21:30 |
| Related URLs: | |
| URI: | https://repository.cshl.edu/id/eprint/39528 |
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