Studies towards the synthesis of the zaragozic acids: Synthesis of the bicyclic acetal core of zaragozic acid C.

被引:30
作者
Paterson, I
Fessner, K
Finlay, MRV
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(97)00885-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The bicyclic core 6 of zaragozic acid C (7) was prepared by the epoxide cyclisation reaction 21 --> 22 --> 15. Acetal 15 was also obtained by acid-promoted rearrangement of the isomeric acetal 19. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:4301 / 4304
页数:4
相关论文
共 18 条
[1]   CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS ;
BHAT, KS ;
ZAIDLEWICZ, M ;
RACHERLA, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392
[2]   Total synthesis of zaragozic acid A (squalestatin S1). Synthesis of the relay compound [J].
Caron, S ;
Stoermer, D ;
Mapp, AK ;
Heathcock, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9126-9134
[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
[8]   USE OF PSEUDOEPHEDRINE AS A PRACTICAL CHIRAL AUXILIARY FOR ASYMMETRIC-SYNTHESIS [J].
MYERS, AG ;
YANG, BH ;
CHEN, H ;
GLEASON, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9361-9362
[9]  
NADIN A, 1996, ANGEW CHEM INT EDIT, V35, P1622
[10]   SYNTHESIS OF ZARAGOZIC ACID A/SQUALESTATIN S1 [J].
NICOLAOU, KC ;
YUE, EW ;
LAGRECA, S ;
NADIN, A ;
YANG, Z ;
LERESCHE, JE ;
TSURI, T ;
NANIWA, Y ;
DERICCARDIS, F .
CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (07) :467-494