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Issue 1, 2016
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A novel C,D-spirodioxene taxoid synthesized through an unexpected Pd-mediated ring cyclization

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Abstract

A novel C,D-spirodioxene taxoid (6) was prepared from paclitaxel (1a), with the key steps including an unexpected Pd-mediated ring cyclization. The anti-tubulin activity of 6 was decreased relative to that of 1a and a previously reported C,D-spirolactone taxane (5). These observations could be rationalized on the basis of molecular modeling results. To the best of our knowledge, this is the first example indicating that 1,4-dioxenes can be synthesized from a mono-allyl vicinal diol through a Wacker-type cyclization. This strategy may be applicable to the synthesis of other C,D-spiro taxoids.

Graphical abstract: A novel C,D-spirodioxene taxoid synthesized through an unexpected Pd-mediated ring cyclization

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Supplementary files

Article information


Submitted
15 Oct 2015
Accepted
18 Nov 2015
First published
25 Nov 2015

Org. Biomol. Chem., 2016,14, 345-352
Article type
Paper

A novel C,D-spirodioxene taxoid synthesized through an unexpected Pd-mediated ring cyclization

S. Wang, P. A. Sánchez-Murcia, F. Gago and W. Fang, Org. Biomol. Chem., 2016, 14, 345
DOI: 10.1039/C5OB02131F

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