(iPrO)3TiCl-induced reactions of α- and β-4(20)-epoxy-5-hydroxytriacetyltaxicin I

被引：12
作者：
Cheng, Q [1 ]
Oritani, T [1 ]
Horiguchi, T [1 ]
机构：
[1] Tohoku Univ, Grad Sch Agr Sci, Div Life Sci, Lab Appl Bioorgan Chem,Aoba Ku, Sendai, Miyagi 981, Japan
来源：
TETRAHEDRON | 1999年 / 55卷 / 41期
基金：
日本学术振兴会;
关键词：
taxoids; epoxides; rearrangements; chlorotitanium trisopropoxide; borno trifluoride;
D O I：
10.1016/S0040-4020(99)00707-3
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chlorolitanium triisopropoxide-induced reaction of alpha-4(20)-epoxy-5-hydroxytriacetyltaxicin I 2 gave a 4-hydroxymethylene-5-one 4 and a 4-hydroxy-4-chloromethylene 5, while the corresponding beta-4(20)-epoxide 3 gave a 3,8-cyclopropane 6 and a 6/8/5 ring system 7. Moreover, boron trifluoride-induced reaction of the a-4(20)epoxide 2 yielded a 6/8/6/7 ring system 8 and an A-ring contracted alcohol derivative 9. Plausible mechanisms of these reactions are proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：12099 / 12108
页数：10
相关论文
共 31 条
[1]   A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE [J].
ADAM, W ;
BIALAS, J ;
HADJIARAPOGLOU, L .
CHEMISCHE BERICHTE, 1991, 124 (10) :2377-2377
[2]  
Adams J D, 1993, J Natl Cancer Inst Monogr, P141
[3]   THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES .14. TAXOIDS FROM THE ROOTS OF TAXUS X MEDIA CV HICKSII [J].
APPENDINO, G ;
CRAVOTTO, G ;
ENRIU, R ;
GARIBOLDI, P ;
BARBONI, L ;
TORREGIANI, E ;
GABETTA, B ;
ZINI, G ;
BOMBARDELLI, E .
JOURNAL OF NATURAL PRODUCTS, 1994, 57 (05) :607-613
[4]   TAXANES FROM TAXUS-BACCATA [J].
APPENDINO, G ;
GARIBOLDI, P ;
PISETTA, A ;
BOMBARDELLI, E ;
GABETTA, B .
PHYTOCHEMISTRY, 1992, 31 (12) :4253-4257
[5]   THE PHYTOCHEMISTRY OF THE YEW TREE [J].
APPENDINO, G .
NATURAL PRODUCT REPORTS, 1995, 12 (04) :349-360
[6]   SYNTHETIC STUDIES TOWARDS TAXOL ANALOGS - CHEMOSELECTIVE CLEAVAGE OF C-5 CINNAMOYL GROUP IN TAXANE GROUP OF DITERPENOIDS WITH HYDROXYLAMINE [J].
BATHINI, Y ;
MICETICH, RG ;
DANESHTALAB, M .
SYNTHETIC COMMUNICATIONS, 1994, 24 (11) :1513-1517
[7]   TAXINE .1. ISOLATION STUDIES AND FUNCTIONAL GROUPS OF O-CINNAMOYLTAXICIN-I [J].
BAXTER, JN ;
TRIPPETT, S ;
LYTHGOE, B ;
SCALES, B ;
SCROWSTON, RM .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (AUG) :2964-+
[8]   X-RAY STRUCTURE OF O-CINNAMOYLTAXICIN-I TRIACETATE, C35H42O10, FROM THE YEW, TAXUS-BACCATA [J].
BEGLEY, MJ ;
FRECKNALL, EA ;
PATTENDEN, G .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1984, 40 (OCT) :1745-1747
[9]  
BISSERY MC, 1991, CANCER RES, V51, P4845
[10]   TOTAL SYNTHESIS OF ANTICANCER AGENT TAXOL ACHIEVED BY 2 DIFFERENT ROUTES [J].
BORMAN, S .
CHEMICAL & ENGINEERING NEWS, 1994, 72 (08) :32-34
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