TY - JOUR
T1 - Canataxpyran A, a novel 3,8-secotaxane with a 13,17-ether bridge from needles of Taxus canadensis
AU - Li, Yong
AU - Zhang, Man Li
AU - Wang, Yu Fang
AU - Dong, Mei
AU - Sauriol, Françoise
AU - Shi, Qing Wen
AU - Kiyota, Hiromasa
AU - Gu, Yu Cheng
AU - Cong, Bin
N1 - Funding Information:
The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (81072551), Key Projects of Science and Technology of Hebei Province (11276103D-89), Scientific Research Foundation for the Returned Overseas Chinese Scholars of Hebei Province (2006-02), and Scientific Research Foundation of Hebei Province (08B032 and C2010000489). We also wish to extend our sincere thanks for the financial support from Syngenta Ltd. (2011-Hebei Medical University-Syngenta-03) and Japan Society for the Promotion of Science (Nos. 19580120 and 22580112).
PY - 2012/4
Y1 - 2012/4
N2 - 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 7 β,9,10 β,20-tetracetoxy-13 β,17-epoxy-3,8-secotaxa-3 E,8 E,11-triene-2 α,5 α -diol (designated as canataxpyran A, 1 ). This bicyclic taxane gradually decomposed in CDCl 3 to give the corresponding enones, 10 β,20-diacetoxy-13 β,17-epoxy-4 α,5 α -dihydroxy-3,8-secotaxa-2 E,7 E,11-trien-9-one (canataxpyran B, 2 ) and 5 α,10 β,20-triacetoxy-13 β,17-epoxy-4 α -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.
AB - 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 7 β,9,10 β,20-tetracetoxy-13 β,17-epoxy-3,8-secotaxa-3 E,8 E,11-triene-2 α,5 α -diol (designated as canataxpyran A, 1 ). This bicyclic taxane gradually decomposed in CDCl 3 to give the corresponding enones, 10 β,20-diacetoxy-13 β,17-epoxy-4 α,5 α -dihydroxy-3,8-secotaxa-2 E,7 E,11-trien-9-one (canataxpyran B, 2 ) and 5 α,10 β,20-triacetoxy-13 β,17-epoxy-4 α -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.
KW - 3,8-secotaxane
KW - Isolation
KW - Needle
KW - Taxaceae
KW - Taxus Canadensis
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U2 - 10.1515/hc-2012-0035
DO - 10.1515/hc-2012-0035
M3 - Article
AN - SCOPUS:84862534659
SN - 0793-0283
VL - 18
SP - 57
EP - 60
JO - Heterocyclic Communications
JF - Heterocyclic Communications
IS - 2
ER -