Studies towards the synthesis of the zaragozic acids: A novel epoxide cyclisation approach to the formation of the bicyclic acetal core.

被引:29
作者
Paterson, I
Fessner, K
Finlay, MRV
Jacobs, MF
机构
[1] University Chemical Laboratory, Cambridge CB2 1EW, Lensfield Road
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(96)02083-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Model studies towards the bicyclic acetal core 1 of the zaragozic acids, based on the epoxide cyclisation reaction 4 --> 3, are described. Epoxide 14 provides the desired bicyclic acetal skeleton 16, while epoxide 27 leads through 28 to an isomeric acetal 30. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:8803 / 8806
页数:4
相关论文
共 22 条
[1]  
ARMSTRONG A, 1995, SYNLETT, P903
[2]   SYNTHESIS OF 1-SUBSTITUTED AND 1,4-DISUBSTITUTED 2,3-DI-O-BENZYL-1,6-ANHYDROGALACTOFURANOSES [J].
CARON, S ;
MCDONALD, AI ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2780-2785
[3]   (+)-ZARAGOZIC-ACID-C - SYNTHESIS AND RELATED STUDIES [J].
CARREIRA, EM ;
DUBOIS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8106-8125
[4]   THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA .1. TAXONOMY, FERMENTATION, ISOLATION, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL-ACTIVITY [J].
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 .
JOURNAL OF ANTIBIOTICS, 1992, 45 (05) :639-647
[5]   THE ISOLATION AND STRUCTURE ELUCIDATION OF ZARAGOZIC ACID-C, A NOVEL POTENT SQUALENE SYNTHASE INHIBITOR [J].
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 .
TETRAHEDRON, 1992, 48 (47) :10221-10226
[6]   ASYMMETRIC-SYNTHESIS OF THE SQUALENE SYNTHASE INHIBITOR ZARAGOZIC ACID-C [J].
EVANS, DA ;
BARROW, JC ;
LEIGHTON, JL ;
ROBICHAUD, AJ ;
SEFKOW, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12111-12112
[7]   PREPARATION AND USE OF TETRA-NORMAL-BUTYLAMMONIUM PER-RUTHENATE (TBAP REAGENT) AND TETRA-NORMAL-PROPYLAMMONIUM PER-RUTHENATE (TPAP REAGENT) AS NEW CATALYTIC OXIDANTS FOR ALCOHOLS [J].
GRIFFITH, WP ;
LEY, SV ;
WHITCOMBE, GP ;
WHITE, AD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (21) :1625-1627
[8]   CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].
KOLB, HC ;
VANNIEUWENHZE, MS ;
SHARPLESS, KB .
CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547
[9]  
NADIN A, 1996, ANGEW CHEM INT EDIT, V35, P1622
[10]   HIGHLY STEREOSELECTIVE AND GENERAL-SYNTHESIS OF (Z)-3-METHYL-2-ALKEN-1-OLS VIA PALLADIUM-CATALYZED CROSS COUPLING OF (Z)-3-IODO-2-BUTEN-1-OL WITH ORGANOZINCS AND OTHER ORGANOMETALS [J].
NEGISHI, E ;
AY, M ;
GULEVICH, YV ;
NODA, Y .
TETRAHEDRON LETTERS, 1993, 34 (09) :1437-1440