CEPHALOSTATIN CHEMISTRY .4. APPLICATION OF THE REICH IODOSO SYN-ELIMINATION FOR THE PREPARATION OF AN INTERMEDIATE APPROPRIATE FOR THE SYNTHESIS OF BOTH HEXACYCLIC STEROIDAL UNITS OF CEPHALOSTATIN-7

被引:23
作者
KIM, SK [1 ]
FUCHS, PL [1 ]
机构
[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907
关键词
D O I
10.1016/0040-4039(94)85350-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hecogenin acetate 5 was converted to an intermediate suitable for construction of both ''North'' and ''South'' hexacyclic spiroketals present in cephalostatin 7. The key chemical transformations involved are: (I)the Reich iodoso syn-elimination of iodide 18; (2) Rhodium [II] catalyzed intermolecular oxygen alkylation of secondary neopentyl alcohol 21; and (3) Intramolecular Wadsworth-Emmons reaction to provide the ester precursor of aldehyde 4.
引用
收藏
页码:7163 / 7166
页数:4
相关论文
共 18 条
  • [1] RHODIUM-CARBENOID MEDIATED O-H INSERTION REACTIONS - O-H INSERTION VS H-ABSTRACTION AND EFFECT OF CATALYST
    COX, GG
    MILLER, DJ
    MOODY, CJ
    SIE, ERHB
    KULAGOWSKI, JJ
    [J]. TETRAHEDRON, 1994, 50 (10) : 3195 - 3212
  • [2] ISOMERIZATION OF ISOSPIROSTANS TO FUROSTENOLS WITH PYRIDINE HYDROCHLORIDE AS THE CATALYST
    DAUBEN, WG
    FONKEN, GJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (18) : 4618 - 4619
  • [3] SYNTHESIS OF A 17-DEOXY, C-14,15-DIHYDRO DERIVATIVE OF THE NORTH SPIROKETAL MOIETY OF THE CEPHALOSTATINS - CONVERSION TO A (+)-TRISDECACYCLIC-C(2) SYMMETRICAL PYRAZINE
    JEONG, JU
    FUCHS, PL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) : 773 - 774
  • [4] JEONG JU, 1994, TETRAHEDRON LETT, V35
  • [5] INTRAMOLECULAR AMINO DELIVERY REACTIONS FOR THE SYNTHESIS OF VALIENAMINE AND ANALOGS
    KNAPP, S
    NAUGHTON, ABJ
    DHAR, TGM
    [J]. TETRAHEDRON LETTERS, 1992, 33 (08) : 1025 - 1028
  • [6] A SHORT ROUTE TO CEPHALOSTATIN ANALOGS
    KRAMER, A
    ULLMANN, U
    WINTERFELDT, E
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (23): : 2865 - 2867
  • [7] LOHRAY BB, 1992, SYNTHESIS-STUTTGART, P1035
  • [8] REACTIONS OF 2,3-EPOXYHALIDES - SYNTHESIS OF OPTICALLY-ACTIVE ALLYLIC ALCOHOLS AND HOMOALLYLIC EPOXIDES
    NICOLAOU, KC
    DUGGAN, ME
    LADDUWAHETTY, T
    [J]. TETRAHEDRON LETTERS, 1984, 25 (20) : 2069 - 2072
  • [9] PAN Y, 1992, BIOORGAN MED CHEM, P967
  • [10] ANTINEOPLASTIC AGENTS .214. ISOLATION AND STRUCTURE OF CEPHALOSTATINS 7-9
    PETTIT, GR
    KAMANO, Y
    INOUE, M
    DUFRESNE, C
    BOYD, MR
    HERALD, CL
    SCHMIDT, JM
    DOUBEK, DL
    CHRISTIE, ND
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) : 429 - 431