Convenient syntheses of (2R,3S,4R)-3-(tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-oxopentanoic acid methoxymethylamide from methacrolein.: Preparation of C1-C7 and C17-C24 fragments of (+)-discodermolide

被引：19

作者：

Day, BW ^{[1
]}

Kangani, CO ^{[1
]}

Avor, KS ^{[1
]}

机构：

[1] Univ Pittsburgh, Sch Pharm, Dept Pharmaceut Sci, Pittsburgh, PA 15261 USA

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(02)00261-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Two new highly stereoselective routes to (2R,3S,4R)-3-(tert-butyldimethylsilanyloxy)-2,4-dimethyl-5-oxopentanoic acid methoxymethylamide, an important intermediate in natural product synthesis, are described. Both schemes are considerably shorter and less expensive than methods previously reported. The title compound was then converted to direct precursors of C1-C7 and C17-24 fragments of the potent microtubule stabilizer (+)-discodermolide. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1161 / 1165

页数：5

共 39 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

[2]

BALACHANDRAN R, 1998, ANTI-CANCER DRUG, V9, P369

[3]

BALACHANDRAN R, 1998, BREAST J, V4, P409

[4] REACTIONS OF CATECHOLBORANE WITH WILKINSON CATALYST - IMPLICATIONS FOR TRANSITION METAL-CATALYZED HYDROBORATIONS OF ALKENES [J].

BURGESS, K ;

VANDERDONK, WA ;

WESTCOTT, SA ;

MARDER, TB ;

BAKER, RT ;

CALABRESE, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9350-9359

[5] MECHANISTIC STUDY OF THE RHODIUM(I)-CATALYZED HYDROBORATION REACTION [J].

EVANS, DA ;

FU, GC ;

ANDERSON, BA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6679-6685

[6] RHODIUM(I)-CATALYZED AND IRIDIUM(I)-CATALYZED HYDROBORATION REACTIONS - SCOPE AND SYNTHETIC APPLICATIONS [J].

EVANS, DA ;

FU, GC ;

HOVEYDA, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6671-6679

[7] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].

EVANS, DA ;

BENDER, SL ;

MORRIS, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526

[8]

GAGE JR, 1990, ORG SYNTH, V68, P77

[9] GENERAL METHODOLOGY FOR THE SYNTHESIS OF CONJUGATED DIENIC INSECT SEX-PHEROMONES [J].

GARDETTE, M ;

JABRI, N ;

ALEXAKIS, A ;

NORMANT, JF .

TETRAHEDRON, 1984, 40 (14) :2741-2750

[10] DISCODERMOLIDE - A NEW BIOACTIVE POLYHYDROXYLATED LACTONE FROM THE MARINE SPONGE DISCODERMIA-DISSOLUTA [J].

GUNASEKERA, SP ;

GUNASEKERA, M ;

LONGLEY, RE ;

SCHULTE, GK .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (16) :4912-4915

← 1 2 3 4 →