1,3-dipolar cycloaddition route to oxygen heterocyclic triones

被引：23
作者：
Jones, RCF
Duller, KAM
Vulto, SIE
机构：
[1] Open Univ, Dept Chem, Milton Keynes MK7 6AA, Bucks, England
[2] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 03期
关键词：
D O I：
10.1039/a707282a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1,3-Dipolar cycloadditon of nitrile oxides, formed in situ by dehydration of primary nitro compounds, with pyrrolidine enamines of protected gamma-hydroxy-beta-keto esters affords isoxazole-4-carboxylates; these are subjected to N-O bond cleavage and lactonisation to afford 3-acyltetronic acids and 3-acyl-4-hydroxytetrahydropyran-2-ones.
引用
收藏
页码：411 / 416
页数：6
相关论文
共 38 条
[1]  
BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857
[2]   MICROBIAL METABOLITES .11. TOTAL SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (S)-CARLOSIC ACID (4-BUTYRYL-2,5-DIHYDRO-3-HYDROXY-5-OXO-FURAN-2-ACETIC ACID) AND CONVERSION OF (R)-5-METHYLTETRONIC ACID INTO (R)-CAROLIC ACID (3,4-DIHYDRO-8-METHYLFURO[3,4-B]OXEPIN-5,6(2H,8H)-DI-ONE) [J].
BLOOMER, JL ;
KAPPLER, FE .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (14) :1485-1491
[3]   ALTERNARIC ACID, A BIOLOGICALLY ACTIVE METABOLIC PRODUCT OF THE FUNGUS ALTERNARIA-SOLANI [J].
BRIAN, PW ;
CURTIS, PJ ;
HEMMING, HG ;
UNWIN, CH ;
WRIGHT, JM .
NATURE, 1949, 164 (4169) :534-534
[4]  
BROUGHTON HB, 1990, J COMPUT AID MOL DES, V4, P5147
[5]   Studies in the biochemistry of micro-organisms. XXXVI. The metabolic products of Penicillium charlesii G. Smith. [J].
Clutterbuck, PW ;
Haworth, WA ;
Raistrick, H ;
Smith, G ;
Stacey, M .
BIOCHEMICAL JOURNAL, 1934, 28 :94-110
[6]  
DAVIES DH, 1981, J CHEM SOC CHEM COMM, P1073, DOI 10.1039/c39810001073
[7]   TOTAL SYNTHESIS OF ELFAMYCINS - AURODOX AND EFROTOMYCIN .1. STRATEGY AND CONSTRUCTION OF KEY INTERMEDIATES [J].
DOLLE, RE ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1691-1694
[8]   TOTAL SYNTHESIS OF ELFAMYCINS - AURODOX AND EFROTOMYCIN .2. COUPLING OF KEY INTERMEDIATES AND COMPLETION OF THE SYNTHESIS [J].
DOLLE, RE ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (06) :1695-1698
[9]   YEAST-CATALYZED REDUCTIVE RING-OPENING OF ISOXAZOLES [J].
EASTON, CJ ;
HUGHES, CM ;
KIRBY, KD ;
SAVAGE, GP ;
SIMPSON, GW ;
TIEKINK, ERT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2035-2035
[10]   TAUTOMERISM IN ACYL TETRONIC ACIDS [J].
GELIN, S ;
POLLET, P .
TETRAHEDRON LETTERS, 1980, 21 (47) :4491-4494
1234