Synthesis of discodermolide intermediates from engineered polyketides

被引：6

作者：

Burlingame, MA ^{[1
]}

Mendoza, E ^{[1
]}

Ashley, GW ^{[1
]}

Myles, DC ^{[1
]}

机构：

[1] Kosan Biosci Inc, Hayward, CA 94545 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 07期

关键词：

D O I：

10.1016/j.tetlet.2005.12.010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Key intermediates used in Smith's total synthesis of discodemolide were synthesized from an engineered polyketide made via precursor feeding to genetically modified polyketide producing bacteria. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：1209 / 1211

页数：3

共 42 条

[1]

[Anonymous], [No title captured], Patent No. 5840750

[2] 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

[3] N-Acyl-2-benzoxazolinones in titanium-mediated Aldol reactions [J].

Burlingame, MA ;

Mendoza, E ;

Ashley, GW .

TETRAHEDRON LETTERS, 2004, 45 (14) :2961-2964

[4] Saccharopolyspora erythraea-catalyzed bioconversion of 6-deoxyerythronolide B analogs for production of novel erythromycins [J].

Carreras, C ;

Frykman, S ;

Ou, S ;

Cadapan, L ;

Zavala, S ;

Woo, E ;

Leaf, T ;

Carney, J ;

Burlingame, M ;

Patel, S ;

Ashley, G ;

Licari, P .

JOURNAL OF BIOTECHNOLOGY, 2002, 92 (03) :217-228

[5] Simplified discodermolide analogues:: Synthesis and biological evaluation of 4-epi-7-dehydroxy-14,16-didemethyl-(+)-discodermolides as microtubule-stabilizing agents [J].

Choy, N ;

Shin, YS ;

Nguyen, PQ ;

Curran, DP ;

Balachandran, R ;

Madiraju, C ;

Day, BW .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :2846-2864

[6] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].

COREY, EJ ;

VENKATESWARLU, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+

[7] Precursor-directed production of erythromycin analogs by Saccharopolyspora erythraea [J].

Frykman, S ;

Leaf, T ;

Carreras, C ;

Licari, P .

BIOTECHNOLOGY AND BIOENGINEERING, 2001, 76 (04) :303-310

[8] 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

[9] CORRECTION [J].

GUNASEKERA, SP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1346-1346

[10] Total synthesis of the potent microtubule-stabilizing agent (+)-discodermolide [J].

Harried, SS ;

Lee, CP ;

Yang, G ;

Lee, TIH ;

Myles, DC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6646-6660

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