HIGH DIASTEREOSELECTION IN THE ALDOL REACTION OF THE BISTRIMETHYLSILYL ENOL ETHER OF METHYL ACETOACETATE WITH 2-BENZYLOXYHEXANAL - SYNTHESIS OF (-)-PESTALOTIN

被引:28
作者
HAGIWARA, H
KIMURA, K
UDA, H
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 06期
关键词
D O I
10.1039/p19920000693
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldol condensation of the bistrimethylsilyl enol ether of methyl acetoacetate, compound 2, with 2-benzyloxyhexanal 3c affords highly selectively (99:1) the syn-aldol adduct 4c in the presence of titanium tetrachloride. The stereocontrolled synthesis of (-)-pestalotin 7 has been achieved.
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页码:693 / 700
页数:8
相关论文
共 50 条
[1]   ZNBR2-MEDIATED HIGHLY DIASTEREOSELECTIVE ADDITION OF GRIGNARD-REAGENTS TO ALPHA-BENZYLOXY ALDEHYDES [J].
ASAMI, M ;
KIMURA, R .
CHEMISTRY LETTERS, 1985, (08) :1221-1222
[2]  
ATRILL RP, 1984, J ORG CHEM, V49, P1679
[3]   REACTIONS OF KETEN ACETALS .7. TOTAL SYNTHESES OF TETRAMETHYL ETHERS OF 1-ACYL-2,4,5,7-TETRAHYDROXYANTHRAQUINONES RHODOLAMPROMETRIN AND RHODOCOMATULIN [J].
BANVILLE, J ;
BRASSARD, P .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (17) :1852-1856
[4]   LEWIS ACID PROMOTED ALDOL ADDITIONS OF ALPHA-THIOSILYLKETENE ACETALS TO ALPHA-ALKOXY ALDEHYDES - DIASTEREOSELECTIVE SYNTHESIS OF SYN-ALPHA-METHYLENE-BETA-HYDROXY-GAMMA-ALKOXY ESTERS [J].
BERNARDI, A ;
CARDANI, S ;
GENNARI, C ;
POLI, G ;
SCOLASTICO, C .
TETRAHEDRON LETTERS, 1985, 26 (52) :6509-6512
[5]   CHEMISTRY OF ENOL SILYL ETHERS - A GENERAL-SYNTHESIS OF 3-HYDROXYHOMOPHTHALATES AND A BIOMIMETIC SYNTHESIS OF SCLERIN .12. [J].
BROWNBRIDGE, P ;
CHAN, TH ;
BROOK, MA ;
KANG, GJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (04) :688-693
[6]  
CARLSON RM, 1974, TETRAHEDRON LETT, P2615
[7]   SYNTHESIS OF 3-OXO-DELTA-LACTONES VIA HETERO-DIELS-ALDER REACTIONS [J].
CASTELLINO, S ;
SIMS, JJ .
TETRAHEDRON LETTERS, 1984, 25 (22) :2307-2310
[8]   INEPT-SI-29 NMR-STUDY OF A TICL4-MEDIATED REACTION OF AN ENOL SILYL ETHER [J].
CHAN, TH ;
BROOK, MA .
TETRAHEDRON LETTERS, 1985, 26 (25) :2943-2946
[9]   TOTAL SYNTHESIS OF BOTH (+)-COMPACTIN AND (+)-MEVINOLIN - A GENERAL STRATEGY BASED ON THE USE OF A SPECIAL TITANIUM REAGENT FOR DICARBONYL COUPLING [J].
CLIVE, DLJ ;
MURTHY, KSK ;
WEE, AGH ;
PRASAD, JS ;
DASILVA, GVJ ;
MAJEWSKI, M ;
ANDERSON, PC ;
EVANS, CF ;
HAUGEN, RD ;
HEERZE, LD ;
BARRIE, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3018-3028
[10]   ON THE SCOPE, MECHANISM, AND STEREOCHEMISTRY OF THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF ACTIVATED DIENES WITH ALDEHYDES - AN APPLICATION TO THE ERYTHRONOLIDE PROBLEM [J].
DANISHEFSKY, SJ ;
LARSON, E ;
ASKIN, D ;
KATO, N .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (05) :1246-1255