THE ASYMMETRIC SYNTHESES OF THE C-1 SIDE-CHAINS OF ZARAGOZIC ACID-A AND ZARAGOZIC ACID-C

被引:29
作者
ROBICHAUD, AJ [1 ]
BERGER, GD [1 ]
EVANS, DA [1 ]
机构
[1] HARVARD UNIV,DEPT CHEM,CAMBRIDGE,MA 02138
关键词
D O I
10.1016/S0040-4039(00)61344-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric syntheses of the C-l sidechains of zaragozic acid A and C are described. Aldol reaction defines the chirality at C-4' and C-5' in two independent routes. Multigram preparation as well as a route amenable to derivatization are highlights of these approaches.
引用
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页码:8403 / 8406
页数:4
相关论文
共 23 条
[1]  
BASHA A, 1977, TETRAHEDRON LETT, P4171
[2]   ZARAGOZIC ACIDS - A FAMILY OF FUNGAL METABOLITES THAT ARE PICOMOLAR COMPETITIVE INHIBITORS OF SQUALENE SYNTHASE [J].
BERGSTROM, JD ;
KURTZ, MM ;
REW, DJ ;
AMEND, AM ;
KARKAS, JD ;
BOSTEDOR, RG ;
BANSAL, VS ;
DUFRESNE, C ;
VANMIDDLESWORTH, FL ;
HENSENS, OD ;
LIESCH, JM ;
ZINK, DL ;
WILSON, KE ;
ONISHI, J ;
MILLIGAN, JA ;
BILLS, G ;
KAPLAN, L ;
OMSTEAD, MN ;
JENKINS, RG ;
HUANG, L ;
MEINZ, MS ;
QUINN, L ;
BURG, RW ;
KONG, YL ;
MOCHALES, S ;
MOJENA, M ;
MARTIN, I ;
PELAEZ, F ;
DIEZ, MT ;
ALBERTS, AW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (01) :80-84
[3]   CHEMOSELECTIVE REMOVAL AND REPLACEMENT OF THE C-4' AND C-6 ACYL ESTERS OF ZARAGOZIC ACID-A [J].
BURK, RM ;
BERGER, GD ;
BUGIANESI, RL ;
GIROTRA, NN ;
PARSONS, WH ;
PONPIPOM, MM .
TETRAHEDRON LETTERS, 1993, 34 (06) :975-978
[4]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[5]  
CHIANG YCP, 1993, IN PRESS BIOMED CHEM, V3
[6]   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
[7]   TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC X-206 [J].
EVANS, DA ;
BENDER, SL ;
MORRIS, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2506-2526
[8]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111
[9]   TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC CYTOVARICIN [J].
EVANS, DA ;
KALDOR, SW ;
JONES, TK ;
CLARDY, J ;
STOUT, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7001-7031
[10]   TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].
EVANS, DA ;
GAGE, JR ;
LEIGHTON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453