A formal synthesis of (+)-discodermolide

被引：17

作者：

Loiseleur, O ^{[1
]}

Koch, G ^{[1
]}

Cercus, J ^{[1
]}

Schürch, F ^{[1
]}

机构：

[1] Novartis Pharma AG, CH-4002 Basel, Switzerland

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2005年 / 9卷 / 03期

关键词：

D O I：

10.1021/op049807s

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Herein, we report the formal synthesis of (+)-discodermolide (1), a promising anticancer agent of sponge origin, in 24 linear steps, with 35 steps in total. The route proceeds from lactone 2, a building block containing the common 1,2-anti-2,3-syn stereotriad found in each of the three subunits, methyl ketone 4 (C-1-C-6), vinyl iodide 7 (C-9--C-14), and iodide 8 (C-15-C-24) utilized for the construction of L The key fragment union was achieved by a Suzuki cross-coupling between 7 and 8.

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页码：259 / 271

页数：13

相关论文

共 70 条

[1]

Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01

[2] OBSERVATION OF CATALYTIC INTERMEDIATES IN THE SUZUKI REACTION BY ELECTROSPRAY MASS-SPECTROMETRY [J].

ALIPRANTIS, AO ;

CANARY, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (15) :6985-6986

[3] TRIMETHYLSILYLATION OF CARBENOIDS GENERATED INSITU FROM ALLYL AND BENZYL HALIDES [J].

ANDRINGA, HH ;

HEUSKLOOS, YA ;

BRANDSMA, L .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 336 (03) :C41-C43

[4]

Arimoto H, 1998, SYNLETT, P765

[5] CONVENIENT GENERAL-METHOD FOR THE PREPARATION OF PRIMARY ALKYLLITHIUMS BY LITHIUM IODINE EXCHANGE [J].

BAILEY, WF ;

PUNZALAN, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) :5404-5406

[6] 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

[7] Stereoselective syntheses of the C1-C5, C7-C15 and C17-C24 fragments of (+)-discodermolide using a catalytic and asymmetric vinylogous mukaiyama reaction [J].

Bazán-Tejeda, B ;

Georgy, M ;

Campagne, JM .

SYNLETT, 2004, (04) :720-722

[8] Stereoselective synthesis of the C1-C13 fragment of (+)-discodermolide using asymmetric allyltitanations [J].

BouzBouz, S ;

Cossy, J .

ORGANIC LETTERS, 2003, 5 (17) :3029-3031

[9] HYDROBORATION .36. DIRECT ROUTE TO 9-BORABICYCLO[3.3.1]NONANE VIA CYCLIC HYDROBORATION OF 1,5-CYCLOOCTADIENE - 9-BORABICYCLO[3.3.1]NONANE AS A UNIQUELY SELECTIVE REAGENT FOR HYDROBORATION OF OLEFINS [J].

BROWN, HC ;

KNIGHTS, EF ;

SCOUTEN, CG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7765-7770

[10] PREPARATION AND USE OF 1-IODOALKYL YLIDES [J].

CHEN, J ;

WANG, T ;

ZHAO, K .

TETRAHEDRON LETTERS, 1994, 35 (18) :2827-2828

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