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

被引：15

作者：

Bazán-Tejeda, B ^{[1
]}

Georgy, M ^{[1
]}

Campagne, JM ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

SYNLETT | 2004年 / 04期

关键词：

asymmetric; lactones; stereoselectivity; catalysis; copper;

D O I：

10.1055/s-2004-817744

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective syntheses of C1-C5, C7-C15 and C17-C24 fragments of (+)-discodermolide are described from a common intermediate: an alpha,beta-unsaturated six-membered lactone obtained in one step using a catalytic and asymmetric vinylogous Mukaiyama (CAVM) reaction.

引用

页码：720 / 722

页数：3

共 22 条

[1] Catalytic asymmetric access to α,β unsaturated δ-lactones through a vinylogous aldol reaction:: Application to the total synthesis of the Prelog-Djerassi lactone [J].

Bluet, G ;

Bazán-Tejeda, B ;

Campagne, JM .

ORGANIC LETTERS, 2001, 3 (23) :3807-3810

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

BouzBouz, S ;

Cossy, J .

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

[3] 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

[4] Formal synthesis of (+)-discodermolide [J].

Francavilla, C ;

Chen, WC ;

Kinder, FR .

ORGANIC LETTERS, 2003, 5 (08) :1233-1236

[5] 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

[6] CORRECTION [J].

GUNASEKERA, SP .

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

[7] 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

[8] Total synthesis of (-)-discodermolide: An application of a chelation-controlled alkylation reaction [J].

Harried, SS ;

Yang, G ;

Strawn, MA ;

Myles, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (18) :6098-6099

[9] Syntheses of discodermolides useful for investigating microtubule binding and stabilization [J].

Hung, DT ;

Nerenberg, JB ;

Schreiber, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (45) :11054-11080

[10]

Kalesse M, 2000, CHEMBIOCHEM, V1, P171, DOI 10.1002/1439-7633(20001002)1:3<171::AID-CBIC171>3.3.CO

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