Chemoenzymatic studies: From cycloheptatriene to the core of zaragozic acids

被引:24
作者
Xu, YP [1 ]
Johnson, CR [1 ]
机构
[1] WAYNE STATE UNIV,DEPT CHEM,DETROIT,MI 48202
关键词
D O I
10.1016/S0040-4039(97)00086-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(1R,4S,6S)-4-Acetoxy-6-triisopropylsilyloxy-2-cyclohepten-1-ol, prepared from cycloheptatriene utilizing an asymmetrization of the precursor diol with Candida antarctica lipase B/isopropenyl acetate, was converted to (1S,3R,4S,5S,6R,7R)-4,6,7-triacetoxy-5-benzyloxymethyl-4- acetoxyethyl-2,8-dioxabicyclo[3.2.1]octane representing the core of zaragozic acid by a strategy involving Rubottom oxidations and ozonolysis. (C) 1997, Elsevier Science Ltd.
引用
收藏
页码:1117 / 1120
页数:4
相关论文
共 18 条
  • [1] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .5. MINOR METABOLITES
    BLOWS, WM
    FOSTER, G
    LANE, SJ
    NOBLE, D
    PIERCEY, JE
    SIDEBOTTOM, PJ
    WEBB, G
    [J]. JOURNAL OF ANTIBIOTICS, 1994, 47 (07) : 740 - 754
  • [2] (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES
    CARREIRA, EM
    DUBOIS, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) : 8106 - 8125
  • [3] SYNTHESIS OF (+)-ZARAGOZIC ACID-C
    CARREIRA, EM
    DUBOIS, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) : 10825 - 10826
  • [4] THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY
    DAWSON, MJ
    FARTHING, JE
    MARSHALL, PS
    MIDDLETON, RF
    ONEILL, MJ
    SHUTTLEWORTH, A
    STYLLI, C
    TAIT, RM
    TAYLOR, PM
    WILDMAN, HG
    BUSS, AD
    LANGLEY, D
    HAYES, MV
    [J]. JOURNAL OF ANTIBIOTICS, 1992, 45 (05) : 639 - 647
  • [5] THE ISOLATION AND STRUCTURE ELUCIDATION OF ZARAGOZIC ACID-C, A NOVEL POTENT SQUALENE SYNTHASE INHIBITOR
    DUFRESNE, C
    WILSON, KE
    ZINK, D
    SMITH, J
    BERGSTROM, JD
    KURTZ, M
    REW, D
    NALLIN, M
    JENKINS, R
    BARTIZAL, K
    TRAINOR, C
    BILLS, G
    MEINZ, M
    HUANG, LY
    ONISHI, J
    MILLIGAN, J
    MOJENA, M
    PELAEZ, F
    [J]. TETRAHEDRON, 1992, 48 (47) : 10221 - 10226
  • [6] ASYMMETRIC-SYNTHESIS OF THE SQUALENE SYNTHASE INHIBITOR ZARAGOZIC ACID-C
    EVANS, DA
    BARROW, JC
    LEIGHTON, JL
    ROBICHAUD, AJ
    SEFKOW, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) : 12111 - 12112
  • [7] HEATHCOCK CH, 1995, 209TH NAT M AM CHEM
  • [8] ENZYMATIC ASYMMETRIZATION IN ORGANIC MEDIA - SYNTHESIS OF UNNATURAL GLUCOSE FROM CYCLOHEPTATRIENE
    JOHNSON, CR
    GOLEBIOWSKI, A
    STEENSMA, DH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) : 9414 - 9418
  • [9] TOTAL SYNTHESES OF ZARAGOZIC ACID
    KOERT, U
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 773 - 778
  • [10] NADIN A, 1996, ANGEW CHEM INT EDIT, V35, P1622