共 81 条
Total synthesis of the potent microtubule-stabilizing agent (+)-discodermolide
被引:53
作者:

Harried, SS
论文数: 0 引用数: 0
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机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

Lee, CP
论文数: 0 引用数: 0
h-index: 0
机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

Yang, G
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机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

Lee, TIH
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h-index: 0
机构: Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

Myles, DC
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h-index: 0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
机构:
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Kosan Biosci, Hayward, CA 94545 USA
关键词:
D O I:
10.1021/jo034521r
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
The total synthesis of the potent microtubule-stabilizing, antimitotic agent (+)-discodermolide is described. The convergent synthetic strategy takes advantage of the diastereoselective alkylation of a ketone enolate to establish the key C15-C16 bond. The synthesis is amenable to preparation of gram-scale quantities of (+)-discodermolide and analogues.
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页码:6646 / 6660
页数:15
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共 81 条
[1]
The potent microtubule-stabilizing agent (+)-discodermolide induces apoptosis in human breast carcinoma cells - preliminary comparisons to paclitaxel
[J].
Balachandran, R
;
ter Haar, E
;
Welsh, MJ
;
Grant, SG
;
Day, BW
.
ANTI-CANCER DRUGS,
1998, 9 (01)
:67-76

Balachandran, R
论文数: 0 引用数: 0
h-index: 0
机构: Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA

ter Haar, E
论文数: 0 引用数: 0
h-index: 0
机构: Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA

Welsh, MJ
论文数: 0 引用数: 0
h-index: 0
机构: Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA

Grant, SG
论文数: 0 引用数: 0
h-index: 0
机构: Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA

Day, BW
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA Univ Pittsburgh, Inst Canc, Pittsburgh, PA 15260 USA
[2]
CATECHOL BORON HALIDES - MILD AND SELECTIVE REAGENTS FOR CLEAVAGE OF COMMON PROTECTING GROUPS
[J].
BOECKMAN, RK
;
POTENZA, JC
.
TETRAHEDRON LETTERS,
1985, 26 (11)
:1411-1414

BOECKMAN, RK
论文数: 0 引用数: 0
h-index: 0

POTENZA, JC
论文数: 0 引用数: 0
h-index: 0
[3]
SIMPLE AND DIRECT SYNTHESIS OF TRANS-1,2-BIS(TRI-NORMAL-BUTYLSTANNYL)ETHYLENE
[J].
BOTTARO, JC
;
HANSON, RN
;
SEITZ, DE
.
JOURNAL OF ORGANIC CHEMISTRY,
1981, 46 (25)
:5221-5222

BOTTARO, JC
论文数: 0 引用数: 0
h-index: 0
机构: NORTHEASTERN UNIV,DEPT MED CHEM,BOSTON,MA 02115

HANSON, RN
论文数: 0 引用数: 0
h-index: 0
机构: NORTHEASTERN UNIV,DEPT MED CHEM,BOSTON,MA 02115

SEITZ, DE
论文数: 0 引用数: 0
h-index: 0
机构: NORTHEASTERN UNIV,DEPT MED CHEM,BOSTON,MA 02115
[4]
A convenient synthesis of dimethyl (diazomethyl)phosphonate (Seyferth Gilbert reagent)
[J].
Brown, DG
;
Velthuisen, EJ
;
Commerford, JR
;
Brisbois, RG
;
Hoye, TR
.
JOURNAL OF ORGANIC CHEMISTRY,
1996, 61 (07)
:2540-2541

Brown, DG
论文数: 0 引用数: 0
h-index: 0
机构:
HAMLINE UNIV,ST PAUL,MN 55104 HAMLINE UNIV,ST PAUL,MN 55104

Velthuisen, EJ
论文数: 0 引用数: 0
h-index: 0
机构:
HAMLINE UNIV,ST PAUL,MN 55104 HAMLINE UNIV,ST PAUL,MN 55104

Commerford, JR
论文数: 0 引用数: 0
h-index: 0
机构:
HAMLINE UNIV,ST PAUL,MN 55104 HAMLINE UNIV,ST PAUL,MN 55104

Brisbois, RG
论文数: 0 引用数: 0
h-index: 0
机构:
HAMLINE UNIV,ST PAUL,MN 55104 HAMLINE UNIV,ST PAUL,MN 55104

Hoye, TR
论文数: 0 引用数: 0
h-index: 0
机构:
HAMLINE UNIV,ST PAUL,MN 55104 HAMLINE UNIV,ST PAUL,MN 55104
[5]
CHIRAL SYNTHESIS VIA ORGANOBORANES .7. DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ERYTHRO-BETA-METHYLOMOALLYL AND THREO-BETA-METHYLHOMOALLYL ALCHOLS VIA ENANTIOMERIC (Z)-CROTYLBORANE AND (E)-CROTYLBORANE
[J].
BROWN, HC
;
BHAT, KS
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1986, 108 (19)
:5919-5923

BROWN, HC
论文数: 0 引用数: 0
h-index: 0

BHAT, KS
论文数: 0 引用数: 0
h-index: 0
[6]
CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY
[J].
BROWN, HC
;
BHAT, KS
;
RANDAD, RS
.
JOURNAL OF ORGANIC CHEMISTRY,
1989, 54 (07)
:1570-1576

BROWN, HC
论文数: 0 引用数: 0
h-index: 0

BHAT, KS
论文数: 0 引用数: 0
h-index: 0

RANDAD, RS
论文数: 0 引用数: 0
h-index: 0
[7]
PREPARATION OF 7-MEMBERED-RING CYCLIC ETHERS AND 3-ALKYLIDENETETRAHYDROPYRANS FROM THE CYCLIZATION OF OXONIUM CATIONS DERIVED FROM UNSUBSTITUTED AND SILICON-CONTAINING 4-ALKEN-1-OLS
[J].
CASTANEDA, A
;
KUCERA, DJ
;
OVERMAN, LE
.
JOURNAL OF ORGANIC CHEMISTRY,
1989, 54 (24)
:5695-5707

CASTANEDA, A
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717 UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

KUCERA, DJ
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717 UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

OVERMAN, LE
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717 UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717
[8]
NI(II)/CR(II)-MEDIATED COUPLING REACTION - AN ASYMMETRIC PROCESS
[J].
CHEN, CP
;
TAGAMI, K
;
KISHI, Y
.
JOURNAL OF ORGANIC CHEMISTRY,
1995, 60 (17)
:5386-5387

CHEN, CP
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138 HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

TAGAMI, K
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138 HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138

KISHI, Y
论文数: 0 引用数: 0
h-index: 0
机构:
HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138 HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138
[9]
STUDIES ON THE ALKYLATION OF CHIRAL ENOLATES - APPLICATION TOWARD THE TOTAL SYNTHESIS OF DISCODERMOLIDE
[J].
CLARK, DL
;
HEATHCOCK, CH
.
JOURNAL OF ORGANIC CHEMISTRY,
1993, 58 (22)
:5878-5879

CLARK, DL
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, University of California, Berkeley

HEATHCOCK, CH
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, University of California, Berkeley
[10]
CHELATION-CONTROLLED FACIALLY SELECTIVE CYCLOCONDENSATION REACTIONS OF CHIRAL ALKOXY ALDEHYDES - SYNTHESES OF A MOUSE ANDROGEN AND OF A CARBON-LINKED DISACCHARIDE
[J].
DANISHEFSKY, SJ
;
PEARSON, WH
;
HARVEY, DF
;
MARING, CJ
;
SPRINGER, JP
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1985, 107 (05)
:1256-1268

DANISHEFSKY, SJ
论文数: 0 引用数: 0
h-index: 0
机构:
MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065 MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065

PEARSON, WH
论文数: 0 引用数: 0
h-index: 0
机构:
MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065 MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065

HARVEY, DF
论文数: 0 引用数: 0
h-index: 0
机构:
MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065 MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065

MARING, CJ
论文数: 0 引用数: 0
h-index: 0
机构:
MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065 MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065

SPRINGER, JP
论文数: 0 引用数: 0
h-index: 0
机构:
MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065 MERCK SHARP & DOHME,DIV RES,RAHWAY,NJ 07065