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.
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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 [J].
COX, GG ;
MILLER, DJ ;
MOODY, CJ ;
SIE, ERHB ;
KULAGOWSKI, JJ .
TETRAHEDRON, 1994, 50 (10) :3195-3212
[2]   ISOMERIZATION OF ISOSPIROSTANS TO FUROSTENOLS WITH PYRIDINE HYDROCHLORIDE AS THE CATALYST [J].
DAUBEN, WG ;
FONKEN, GJ .
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 [J].
JEONG, JU ;
FUCHS, PL .
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 [J].
KNAPP, S ;
NAUGHTON, ABJ ;
DHAR, TGM .
TETRAHEDRON LETTERS, 1992, 33 (08) :1025-1028
[6]   A SHORT ROUTE TO CEPHALOSTATIN ANALOGS [J].
KRAMER, A ;
ULLMANN, U ;
WINTERFELDT, E .
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 [J].
NICOLAOU, KC ;
DUGGAN, ME ;
LADDUWAHETTY, T .
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 [J].
PETTIT, GR ;
KAMANO, Y ;
INOUE, M ;
DUFRESNE, C ;
BOYD, MR ;
HERALD, CL ;
SCHMIDT, JM ;
DOUBEK, DL ;
CHRISTIE, ND .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :429-431