Naomi A. Barton
Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?
Barton, Naomi A.; Marsh, Benjamin J.; Lewis, William; Narraidoo, Nathalie; Seymour, Graham B.; Fray, Rupert George; Hayes, Christopher J.
Benjamin J. Marsh
William Lewis 0000-0001-7103-6981
Professor GRAHAM SEYMOUR firstname.lastname@example.org
Professor of Plant Biotechnology
Rupert George Fray
CHRIS HAYES email@example.com
Professor of Organic Chemistry
We have shown for the first time that taxadiene (3) can be epoxidised in a regio- and diastereoselective manner to provide taxadiene-4(5)-epoxide (12) as a single diastereoisomer, and that this epoxide can be rearranged to give taxa-4(20),11(12)-dien-5α-ol (4). Furthermore, the epoxide 12 rearranges under acidic conditions to give taxa-4(20),11(12)-dien-5α-ol (4), the known bridged ether OCT (5) and the new oxacyclotaxane (OCT2) 15. Contrary to previous speculation, taxadiene-4(5)-epoxide (12) is susceptible to rearrangement when exposed to an ironIII porphyrin, and these observations justify consideration of epoxide 12 as a chemically competent intermediate on the taxol biosynthetic pathway.
|Journal Article Type||Article|
|Publisher||Royal Society of Chemistry|
|Peer Reviewed||Peer Reviewed|
|APA6 Citation||Barton, N. A., Marsh, B. J., Lewis, W., Narraidoo, N., Seymour, G. B., Fray, R. G., & Hayes, C. J. (in press). Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?. Chemical Science, 7(5), https://doi.org/10.1039/c5sc03463a|
|Copyright Statement||Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0|
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0
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