INTRAMOLECULAR ACYL MIGRATIONS IN TAXANES FROM TAXUS-BREVIFOLIA

被引：28
作者：
CHU, A
DAVIN, LB
ZAJICEK, J
LEWIS, NG
CROTEAU, R
机构：
[1] WASHINGTON STATE UNIV,INST BIOL CHEM,467 CLARK HALL,PULLMAN,WA 99164
[2] WASHINGTON STATE UNIV,CTR NMR SPECT,PULLMAN,WA 99164
来源：
PHYTOCHEMISTRY | 1993年 / 34卷 / 02期
基金：
美国国家卫生研究院;
关键词：
TAXUS-BREVIFOLIA; TAXACEAE; YEW; BARK; DITERPENOIDS; TAXOL; TAXANES; 1-BETA-HYDROXYBACCATIN-I; ACYL GROUP MIGRATION;
D O I：
10.1016/0031-9422(93)80033-O
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Two new taxane epoxides were isolated from the bark of Taxus brevifolia and their structures were established as 1beta,9alpha-dihydroxy-4beta,20-epoxy-2alpha,5alpha,7beta,10beta,13alpha-pentaacetoxy-tax-11-ene and 1beta,7beta-dihydroxy-4beta,20-epoxy-2alpha,5alpha,9alpha,10beta,13alpha-pentaacetoxy-tax-11-ene. These two compounds were found to readily isomerize via acyl migration upon standing in CDCl3 solution and represent the first example of intramolecular transesterification in this large family of taxane metabolites.
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页码：473 / 476
页数：4
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