Azadiene Diels-Alder reactions: Scope and applications. Total synthesis of natural and ent-fredericamycin A

被引:45
作者
Boger, DL
机构
[1] Department of Chemistry, Scripps Research Institute, San Diego, CA 92037
关键词
D O I
10.1002/jhet.5570330508
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A review of our studies of the inverse electron demand Diels-Alder reactions of heteroaromatic and acyclic azadienes is presented and the application of a N-sulfonyl-1-aza-1,3-butadiene [4 + 2] cycloaddition reaction in the total synthesis of natural and ent-fredericamycin A is described in detail.
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页码:1519 / 1531
页数:13
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共 74 条
[1]  
[Anonymous], 1989, PROG HET CH
[2]   THE DIELS-ALDER REACTION OF 1-VINYLNAPHTHALENE WITH ALPHA,BETA-UNSATURATED AND ALPHA,BETA,GAMMA,DELTA-UNSATURATED ACIDS AND DERIVATIVES [J].
BACHMANN, WE ;
DENO, NC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (09) :3062-3072
[3]  
Boger D. L., 1987, HETERO DIELS ALDER M
[4]   TOTAL SYNTHESIS OF PRODIGIOSIN, PRODIGIOSENE, AND DESMETHOXYPRODIGIOSIN - DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES AND DEVELOPMENT OF AN EFFECTIVE PALLADIUM(II)-PROMOTED 2,2'-BIPYRROLE COUPLING PROCEDURE [J].
BOGER, DL ;
PATEL, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1405-1415
[5]   TOTAL SYNTHESIS OF (-)-PYRIMIDOBLAMIC ACID AND DEGLYCOBLEOMYCIN A2 [J].
BOGER, DL ;
MENEZES, RF ;
HONDA, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (02) :273-275
[6]   TOTAL SYNTHESES OF (+)-P-3A, EPI-(-)-P-3A, AND (-)-DESACETAMIDO P-3A [J].
BOGER, DL ;
HONDA, T ;
MENEZES, RF ;
COLLETTI, SL ;
DANG, Q ;
YANG, WJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (01) :82-92
[7]   TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .3. SYNTHESIS AND COMPARATIVE-EVALUATION OF DEGLYCOBLEOMYCIN-A(2), EPIDEGLYCOBLEOMYCIN-A(2), DEGLYCOBLEOMYCIN-A(1), AND DESACETAMIDODEGLYCOBLEOMYCIN, DESCARBOXAMIDODEGLYCOBLEOMYCIN, DESMETHYLDEGLYCOBLEOMYCIN, AND DESIMIDAZOLYLDEGLYCOBLEOMYCIN-A(2) [J].
BOGER, DL ;
HONDA, T ;
MENEZES, RF ;
COLLETTI, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5631-5646
[8]  
BOGER DL, 1990, B SOC CHIM BELG, V99, P599
[9]   A DETAILED, CONVENIENT PREPARATION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE [J].
BOGER, DL ;
COLEMAN, RS ;
PANEK, JS ;
HUBER, FX ;
SAUER, J .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5377-5379
[10]   THERMAL CYCLOADDITION OF DIMETHYL "1,2,4,5-TETRAZINE-3,6-DICARBOXYLATE WITH ELECTRON-RICH OLEFINS - 1,2-DIAZINE AND PYRROLE INTRODUCTION - PREPARATION OF OCTAMETHYLPORPHIN (OMP) [J].
BOGER, DL ;
COLEMAN, RS ;
PANEK, JS ;
YOHANNES, D .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4405-4409