Total synthesis of streptonigrone

被引：52

作者：

Chan, Bryan K. ^{[1
]}

Ciufolini, Marco A. ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 22期

关键词：

D O I：

10.1021/jo701435p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad - Limpach reaction, rather than the customary Friedlander methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.

引用

页码：8489 / 8495

页数：7

共 59 条

[1]

[Anonymous], TARGETS HETEROCYCLIC

[2] TOTAL SYNTHESIS OF STREPTONIGRIN [J].

BASHA, FZ ;

HIBINO, S ;

KIM, D ;

PYE, WE ;

WU, TT ;

WEINREB, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3962-3964

[3] Highly efficient and practical syntheses of lavendamycin methyl ester and related novel quinolindiones [J].

Behforouz, M ;

Haddad, J ;

Cai, W ;

Arnold, MB ;

Mohammadi, F ;

Sousa, AC ;

Horn, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (19) :6552-6555

[4] SYNTHESIS OF (ALPHA,ALPHA-DIFLUOROALKYL)PHOSPHONATES BY DISPLACEMENT OF PRIMARY TRIFLATES [J].

BERKOWITZ, DB ;

EGGEN, M ;

SHEN, Q ;

SLOSS, DG .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6174-6176

[5]

Boger D., 1996, CHEMTRACTS ORG CHEM, V9, P149

[6]

Boger D.L., 1988, STRATEGIES TACTICS O, V2, P1

[7] TOTAL SYNTHESIS OF LAVENDAMYCIN METHYL-ESTER [J].

BOGER, DL ;

DUFF, SR ;

PANEK, JS ;

YASUDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5790-5795

[8] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].

BOGER, DL .

CHEMICAL REVIEWS, 1986, 86 (05) :781-793

[9] TOTAL SYNTHESIS OF STREPTONIGRONE [J].

BOGER, DL ;

CASSIDY, KC ;

NAKAHARA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :10733-10741

[10] STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES [J].

BOGER, DL ;

YASUDA, M ;

MITSCHER, LA ;

DRAKE, SD ;

KITOS, PA ;

THOMPSON, SC .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1918-1928

← 1 2 3 4 5 6 →