Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?

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Barton, Naomi A., Marsh, Benjamin J., Lewis, William, Narraidoo, Nathalie, Seymour, Graham B., Fray, Rupert George and Hayes, Christopher J. (2016) Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway? Chemical Science, 7 (5). pp. 3102-3107. ISSN 2041-6539

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Abstract

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.

Item Type: Article
RIS ID: https://nottingham-repository.worktribe.com/output/771607
Schools/Departments: University of Nottingham, UK > Faculty of Science > School of Biosciences > Division of Plant and Crop Sciences
University of Nottingham, UK > Faculty of Science > School of Chemistry
Identification Number: https://doi.org/10.1039/c5sc03463a
Depositing User: Fray, Rupert
Date Deposited: 10 Oct 2016 13:47
Last Modified: 04 May 2020 17:30
URI: https://eprints.nottingham.ac.uk/id/eprint/37455

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