SYNTHESIS OF RING-B REARRANGED TAXANE ANALOGS

被引：25

作者：

KLEIN, LL ^{[1
]}

MARING, CJ ^{[1
]}

LI, LP ^{[1
]}

YEUNG, CM ^{[1
]}

THOMAS, SA ^{[1
]}

GRAMPOVNIK, DJ ^{[1
]}

PLATTNER, JJ ^{[1
]}

HENRY, RF ^{[1
]}

机构：

[1] ABBOTT LABS,DIV ANALYT RES,ABBOTT PK,IL 60064

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 09期

关键词：

D O I：

10.1021/jo00088a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of the C-7 hydroxyl group on the 9-dihydrotaxane skeleton with triflic anhydride causes a major skeletal rearrangement to occur leading to contraction of ring B. In addition the formation of a ring C-fused cyclopropane structure occurs. The requisite C-13 phenylisoserinate side chains are appended via an initial deacylation of the C-13 acetate followed by reacylation and deprotection. These rearranged compounds show very similar structural features with the parent 9-dihydrotaxane skeleton and also retain biological activity.

引用

页码：2370 / 2373

页数：4

共 20 条

[1]

CHAN WR, 1966, J CHEM SOC CHEM COMM, P923

[2] MODIFIED TAXOLS .10. PREPARATION OF 7-DEOXYTAXOL, A HIGHLY BIOACTIVE TAXOL DERIVATIVE, AND INTERCONVERSION OF TAXOL AND 7-EPI-TAXOL [J].