AN INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION/ELECTROPHILIC CYCLIZATION SEQUENCE TO GIVE CYCLIC ETHERS

被引:23
作者
BEEBE, X [1 ]
CHIAPPARI, CL [1 ]
KURTH, MJ [1 ]
SCHORE, NE [1 ]
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
关键词
D O I
10.1021/jo00078a003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An intramolecular 1,3-dipolar cycloaddition/electrophilic cyclization sequence has been developed for the synthesis of cyclic ethers. This approach utilizes a diastereoselective nitrile oxide 1,3-dipolar cycloaddition to give furoisoxazoles, which undergo subsequent electrophilic cyclization to afford substituted tetrahydrofurans.
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页码:7320 / 7321
页数:2
相关论文
共 23 条
[1]   POLYMER-SUPPORTED SYNTHESIS OF 2,5-DISUBSTITUTED TETRAHYDROFURANS [J].
BEEBE, X ;
SCHORE, NE ;
KURTH, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :10061-10062
[3]   REDUCTION OF SUBSTITUTED DELTA-2-ISOXAZOLINES - SYNTHESIS OF BETA-HYDROXY ACID-DERIVATIVES [J].
CURRAN, DP ;
SCANGA, SA ;
FENK, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19) :3474-3478
[4]   THE ISOLATION AND STRUCTURE OF CP-120,509, A NEW POLYETHER ANTIBIOTIC RELATED TO SEMDURAMICIN AND PRODUCED BY MUTANTS OF ACTINOMADURA-ROSEORUFA [J].
DIRLAM, JP ;
BORDNER, J ;
CHANG, SP ;
GRIZZUTI, A ;
NELSON, TH ;
TYNAN, EJ ;
WHIPPLE, EB .
JOURNAL OF ANTIBIOTICS, 1992, 45 (09) :1544-1548
[5]   THE STRUCTURE OF CP-80,219, A NEW POLYETHER ANTIBIOTIC RELATED TO DIANEMYCIN [J].
DIRLAM, JP ;
PRESSEAULINABURY, L ;
KOSS, DA .
JOURNAL OF ANTIBIOTICS, 1990, 43 (06) :727-730
[6]   LITHIUM, POTASSIUM, AND SODIUM ALKOXIDES - DONORS IN THE MICHAEL ADDITION-REACTION OF ALPHA-NITROOLEFINS [J].
DUFFY, JL ;
KURTH, JA ;
KURTH, MJ .
TETRAHEDRON LETTERS, 1993, 34 (08) :1259-1260
[7]   SYNTHETIC STUDIES IN THE LYSOCELLIN FAMILY OF POLYETHER ANTIBIOTICS - THE TOTAL SYNTHESIS OF FERENSIMYCIN-B [J].
EVANS, DA ;
POLNIASZEK, RP ;
DEVRIES, KM ;
GUINN, DE ;
MATHRE, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7613-7630
[8]  
EVANS DA, 1990, J AM CHEM SOC, V112, P8590
[9]   MECHANISM OF HYDRIDE REDUCTION OF 1-ALKYN-3-OLS [J].
GRANT, B ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :968-970
[10]   CYCLO-ADDITIONS .41. CONVERSION OF UNSATURATED ALCOHOLS INTO FUNCTIONALIZED TETRAHYDROFURANS AND TETRAHYDROPYRANS VIA NITRILE OXIDE DIPOLAR CYCLO-ADDITIONS [J].
HASSNER, A ;
MURTHY, KSK ;
PADWA, A ;
CHIACCHIO, U ;
DEAN, DC ;
SCHOFFSTALL, AM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5277-5286