ASYMMETRIC-SYNTHESIS OF MACBECIN-I

被引:50
作者
EVANS, DA
MILLER, SJ
ENNIS, MD
ORNSTEIN, PL
机构
[1] Department of Chemistry, Harvard University, Cambridge
关键词
D O I
10.1021/jo00030a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric synthesis of macbecin I is described wherein the absolute stereochemical relationships were established through the use of chiral boron aldol bond constructions and internally directed alpha-methoxy ketone reduction, while the E,Z dienic amide moiety was installed in one step using a vinylogous phosphonate reagent.
引用
收藏
页码:1067 / 1069
页数:3
相关论文
共 32 条
  • [1] TOTAL SYNTHESIS OF (+)-MACBECIN-I
    BAKER, R
    CASTRO, JL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01): : 47 - 65
  • [2] BASHA A, 1977, TETRAHEDRON LETT, P4171
  • [3] BUTCHTA E, 1960, CHEM BER, V93, P1349
  • [4] COREY EJ, 1975, SYNTHESIS-STUTTGART, P590
  • [5] GELDANAMYCIN, A NEW ANTIBIOTIC
    DEBOER, C
    MEULMAN, PA
    WNUK, RJ
    PETERSON, DH
    [J]. JOURNAL OF ANTIBIOTICS, 1970, 23 (09) : 442 - &
  • [6] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
    DESS, DB
    MARTIN, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287
  • [7] DIAGOMESEGUER J, 1980, SYNTHESIS-STUTTGART, P547
  • [8] OXONIUM SALT ALKYLATION OF STRUCTURALLY AND OPTICALLY LABILE ALCOHOLS
    DIEM, MJ
    BUROW, DF
    FRY, JL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) : 1801 - 1802
  • [9] ENNIS MD, 1983, THESIS CALTECH
  • [10] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC IONOMYCIN
    EVANS, DA
    DOW, RL
    SHIH, TL
    TAKACS, JM
    ZAHLER, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) : 5290 - 5313