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A novel 6/12-membered bicyclic taxane with a 13,17-ether bridge, named canataxpyran A, was isolated from the needles of  Taxus canadensis . The structures were characterized as 7β,9,10β,20-tetracetoxy-13β,17-epoxy-3,8-secotaxa-3 E ,8 E ,11-triene-2α,5α-diol (designated as canataxpyran A,  1 ). This bicyclic taxane gradually decomposed in CDCl 3 to give the corresponding enones, 10β,20-diacetoxy-13β,17-epoxy-4α,5α-dihydroxy-3,8-secotaxa-2 E ,7 E ,11-trien-9-one (canataxpyran B,  2 ) and 5α,10β,20-triacetoxy-13β,17-epoxy-4α-hydroxy- 3,8-secotaxa-2 E ,7 E ,11-trien-9-one (canataxpyran C,  3 ). Compound  1  is the first example of a natural 3,8-secotaxane with 13,17-oxygen bridge.

Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis