Taxus canadensis taxanes: structures and stereochemistry

Abstract

The structures and stereochemistry of 14 taxanes isolated from Taxuscanadensis have been rigorously established by high-resolution NMR techniques and mass spectrometry. Taxuscanadensis is the only yew that accumulates 9-dihydro-13-acetylbaccatin III (also called 7,9-deacetylbaccatin VI) as the most abundant taxane. Five 9-dihydrotaxanes derived from the Canadian yew are novel natural products not reported in the needles of other species of yew (8–11, 14, Fig. 1). Keywords: Taxuscanadensis, Taxaceae, taxanes, 9-dihydro-13-acetylbaccatin III, taxol.