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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.

Authors

Naomi A. Barton

Benjamin J. Marsh

William Lewis 0000-0001-7103-6981

Nathalie Narraidoo

Rupert George Fray

CHRIS HAYES chris.hayes@nottingham.ac.uk
Professor of Organic Chemistry



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.

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

Journal Article Type Article
Acceptance Date Jan 26, 2016
Online Publication Date Jan 26, 2016
Deposit Date Oct 10, 2016
Publicly Available Date Oct 10, 2016
Journal Chemical Science
Print ISSN 2041-6520
Electronic ISSN 2041-6539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 7
Issue 5
DOI https://doi.org/10.1039/c5sc03463a
Public URL http://eprints.nottingham.ac.uk/id/eprint/37455
Publisher URL http://pubs.rsc.org/en/Content/ArticleLanding/2016/SC/C5SC03463A#
Copyright Statement Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0

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Copyright Statement
Copyright information regarding this work can be found at the following address: http://creativecommons.org/licenses/by/4.0





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