@article { , title = {Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?}, 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-5?-ol (4). Furthermore, the epoxide 12 rearranges under acidic conditions to give taxa-4(20),11(12)-dien-5?-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.}, doi = {10.1039/c5sc03463a}, eissn = {2041-6539}, issn = {2041-6520}, issue = {5}, journal = {Chemical Science}, publicationstatus = {Published}, publisher = {Royal Society of Chemistry}, url = {https://nottingham-repository.worktribe.com/output/771607}, volume = {7}, author = {Barton, Naomi A. and Marsh, Benjamin J. and Lewis, William and Narraidoo, Nathalie and Seymour, Graham B. and Fray, Rupert George and Hayes, Christopher J.} }