Syntheses of new fluorine-containing taxoids by means of beta-lactam synthon method

被引：48

作者：

Ojima, I

Kuduk, SD

Slater, JC

Gimi, RH

Sun, CM

机构：

[1] Department of Chemistry, State University of New York at Stony Brook, Stony Brook

来源：

TETRAHEDRON | 1996年 / 52卷 / 01期

关键词：

D O I：

10.1016/0040-4020(95)00865-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of new fluorine-containing analogs of paclitaxel and docetaxel are synthesized using the coupling of (3R,4S)-1-acyl-beta-lactams with high enantiomeric purity with properly protected baccatin III, 10-deacetylbaccatin III, and 14 beta-hydroxy-10-deacetylbaccatin III as the key step (beta-Lactam Synthon Method). (3R,4S)-1-Acyl-beta-lactams are prepared through efficient chiral ester enolate - imine cyclocondensation.

引用

页码：209 / 224

页数：16

共 27 条

[1]

[Anonymous], 1995, ADV ASYMMETRIC SYNTH

[2] 14-BETA-HYDROXY-10-DEACETYLBACCATIN-III, A NEW TAXANE FROM HIMALAYAN YEW (TAXUS-WALLICHIANA ZUCC) [J].

APPENDINO, G ;

GARIBOLDI, P ;

GABETTA, B ;

PACE, R ;

BOMBARDELLI, E ;

VITERBO, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (21) :2925-2929

[3] TAXOL(R) STRUCTURE-ACTIVITY-RELATIONSHIPS - SYNTHESIS AND BIOLOGICAL EVALUATION OF TAXOL ANALOGS MODIFIED AT C-7 [J].

CHEN, SH ;

KANT, J ;

MAMBER, SW ;

ROTH, GP ;

WEI, JM ;

MARSHALL, D ;

VYAS, DM ;

FARINA, V ;

CASAZZA, A ;

LONG, BH ;

ROSE, WC ;

JOHNSTON, K ;

FAIRCHILD, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (18) :2223-2228

[4]

Chen Shu-Hui, 1995, V583, P247

[5] A HIGHLY EFFICIENT, PRACTICAL APPROACH TO NATURAL TAXOL [J].

DENIS, JN ;

GREENE, AE ;

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

MANGATAL, L ;

POTIER, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (17) :5917-5919

[6]

Filler R., 1993, ORGANOFLUORINE COMPO, V48

[7]

GEORG GI, 1995, ACS SYM SER, V583, P217

[8] AN EFFICIENT SEMISYNTHESIS OF TAXOL FROM (3R,4S)-N-BENZOYL-3-[(T-BUTYLDIMETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE AND 7-(TRIETHYLSILYL)BACCATIN III [J].

GEORG, GI ;

CHERUVALLATH, ZS ;

HARRIMAN, GCB ;

HEPPERLE, M ;

PARK, H .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (11) :2467-2470

[9]

GEORG GI, 1995, TAXAME ANTICANCER AG

[10] TAXOL AND TAXOTERE - DISCOVERY, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].

GUENARD, D ;

GUERITTEVOEGELEIN, F ;

POTIER, P .

ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) :160-167

← 1 2 3 →