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

Chemical Science
Naomi A BartonChristopher J Hayes

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.

References

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Citations

Mar 23, 2018·Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe·Aparajita Banerjee, Björn Hamberger
Sep 7, 2017·Biotechnology and Applied Biochemistry·Laxmi Sagwan-Barkdoll, Aldwin M Anterola
Oct 14, 2021·Journal of the American Chemical Society·Ya-Jian HuChuang-Chuang Li

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Methods Mentioned

BETA
column chromatography
X-ray
NMR

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