SYNTHESIS OF A RING-A PRECURSOR OF DOXORUBICIN - STEREOSELECTIVE CONTROL OF THE EPOXIDATION OF A HOMOALLYLIC ALCOHOL BY HYDROXYL AND ESTER GROUPS

被引：9

作者：

CHAMBERLAIN, T ^{[1
]}

FU, XP ^{[1
]}

PECHACEK, JT ^{[1
]}

XIN, P ^{[1
]}

WHEELER, DMS ^{[1
]}

WHEELER, MM ^{[1
]}

机构：

[1] UNIV NEBRASKA,DEPT CHEM,LINCOLN,NE 68588

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 14期

关键词：

D O I：

10.1016/S0040-4039(00)74309-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The key step in a synthesis of a precursor for ring A in doxorubicin is the stereoselective control of the epoxidation of a homoallylic alcohol by ester and hydroxyl groups; the result leads to a new method of forming lactones in excellent yields under neutral conditions.

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页码：1707 / 1710

页数：4

相关论文

共 18 条

[1] A NEW ROUTE TO 3-HYDROXYPHTHALIDES - APPLICATION TO THE SYNTHESIS OF RACEMIC [5-C-13] DAUNOMYCINONE [J].

BECKER, AM ;

IRVINE, RW ;

MCCORMICK, AS ;

RUSSELL, RA ;

WARRENER, RN .

TETRAHEDRON LETTERS, 1986, 27 (29) :3431-3434

[2] RE-EXAMINATION OF SODIUM AND LIQUID-AMMONIA REDUCTION OF META METHOXYBENZOIC ACID [J].

BIFFIN, MEC ;

MORITZ, AG ;

PAUL, DB .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (06) :1329-&

[3] ANTHRACYCLINONES .3. CHIRAL POOL SYNTHESIS OF ANTHRACYCLINONES VIA TETRALIN INTERMEDIATES [J].

GENOT, A ;

FLORENT, JC ;

MONNERET, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (06) :1057-1063

[4] ORGANOCERIUM REAGENTS - NUCLEOPHILIC-ADDITION TO EASILY ENOLIZABLE KETONES [J].

IMAMOTO, T ;

SUGIURA, Y ;

TAKIYAMA, N .

TETRAHEDRON LETTERS, 1984, 25 (38) :4233-4236

[5] CARBON CARBON BOND-FORMING REACTIONS USING CERIUM METAL OR ORGANOCERIUM(III) REAGENTS [J].

IMAMOTO, T ;

KUSUMOTO, T ;

TAWARAYAMA, Y ;

SUGIURA, Y ;

MITA, T ;

HATANAKA, Y ;

YOKOYAMA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3904-3912

[6] ALLYLIC VS HOMOALLYLIC CONTROL OF STEREOSPECIFICITY IN THE EPOXIDATION OF 3(1'-HYDROXYETHYL)-5,8-DIMETHOXY-1,2-DIHYDRONAPHTHALEN-1-OL - IMPLICATIONS FOR THE SYNTHESIS OF CHIRAL ANTHRACYCLINES [J].

IRVINE, RW ;

RUSSELL, RA ;

WARRENER, RN .

TETRAHEDRON LETTERS, 1985, 26 (49) :6117-6120

[7] 1,2-FUNCTIONALIZATION OF ALPHA,BETA-EPOXYCYCLOALKANONES [J].

KANG, J ;

KIM, DH ;

LEE, JH ;

RIM, JG ;

YOON, YB ;

KIM, KJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5555-5558

[8]

KENO S, 1980, HETEROCYCLES, V14, P661

[9]

KROHN K, 1990, TETRAHEDRON, V46, P291

[10] TOTAL SYNTHESIS OF ANTHRACYCLINONE [J].

KROHN, K .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (09) :790-807