BIOSYNTHESIS OF COLLETODIOL AND RELATED POLYKETIDE MACRODIOLIDES IN CYTOSPORA SP - ATCC 20502 - SYNTHESIS AND METABOLISM OF ADVANCED INTERMEDIATES

被引:22
作者
ONEILL, JA [1 ]
SIMPSON, TJ [1 ]
WILLIS, CL [1 ]
机构
[1] UNIV BRISTOL,SCH CHEM,CANTOCKS CLOSE,BRISTOL BS8 1TS,AVON,ENGLAND
关键词
D O I
10.1039/c39930000738
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The triene 3 and epoxide 6 have been synthesised in specifically labelled form and their incorporation into the macrodiolide, colletodiol 1 demonstrated in cultures of Cytospora sp. ATCC 20502; results of a biomimetic reaction indicate that both colletoketol 2 and grahamimycin A1 7 may be biosynthesised in a single oxidation step from colletodiol.
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页码:738 / 740
页数:3
相关论文
共 20 条
  • [1] SULFOXONIUM SALTS AS REAGENTS FOR OXIDATION OF PRIMARY AND SECONDARY ALCOHOLS TO CARBONYL-COMPOUNDS
    ALBRIGHT, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (13) : 1977 - 1979
  • [2] REVISED STRUCTURE OF THE MACRODIOLIDE COLLETODIOL
    AMSTUTZ, R
    HUNGERBUHLER, E
    SEEBACH, D
    [J]. HELVETICA CHIMICA ACTA, 1981, 64 (06) : 1796 - 1799
  • [3] BALDWIN JE, 1992, SYNLETT, P875
  • [4] BOCKMAN R, 1974, J AM CHEM SOC, V96, P5954
  • [5] TOTAL SYNTHESIS OF THE MACRODIOLIDE PYRENOPHOROL
    DOMMERHOLT, FJ
    THIJS, L
    ZWANENBURG, B
    [J]. TETRAHEDRON LETTERS, 1991, 32 (11) : 1499 - 1502
  • [6] AN ENANTIOSELECTIVE TOTAL SYNTHESIS OF THE MACRODIOLIDE (-)-(RRR)-COLLETALLOL
    DOMMERHOLT, FJ
    THIJS, L
    ZWANENBURG, B
    [J]. TETRAHEDRON LETTERS, 1991, 32 (11) : 1495 - 1498
  • [7] GAREGG PJ, 1979, SYNTHESIS-STUTTGART, P469
  • [8] GUNTER C, UNPUB
  • [9] GURUSIDDAIAH S, 1981, ANTIMICROB AGENTS CH, V19, P1953
  • [10] TOTAL SYNTHESIS OF (-)-GRAHAMIMYCIN-A1
    HILLIS, LR
    RONALD, RC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (04) : 470 - 473