ENANTIOSELECTIVE SYNTHESIS OF THE AB RING-SYSTEM OF AKLAVINONE VIA A CHEMOENZYMATIC ROUTE

被引:10
作者
GUANTI, G [1 ]
RIVA, R [1 ]
机构
[1] CNR,CTR STUDIO CHIM COMPOSTI CICLOALIFAT & AROMAT,I-16132 GENOA,ITALY
关键词
D O I
10.1016/0040-4039(95)00645-S
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The AB ring system 2 of aklavinone 1 was obtained using a chemoenzymatic protocol. Key steps are the stereoselective addition of lithium enolate of ethyl acetate to ketone 13 and the intramolecular Friedel-Crafts reaction to give tetralin 17.
引用
收藏
页码:3933 / 3936
页数:4
相关论文
共 18 条
[1]  
ADLINGTON MG, 1976, TETRAHEDRON LETT, V34, P2955
[2]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[3]   RHODOMYCINE .X. ANTIBIOTICA AUS ACTINOMYCENTEN .53. ALPHA-RHODOMYCINON BETA1-RHODOMYCINON 10-DESOXY-GAMMA-RHODOMYCINON [J].
BROCKMANN, H ;
NIEMEYER, J ;
BROCKMAN.H ;
BUDZIKIE.H .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (12) :3785-+
[4]   ENZYMATIC ASYMMETRIZATION OF SOME PROCHIRAL AND MESO DIOLS THROUGH MONOACETYLATION WITH PIG PANCREATIC LIPASE (PPL) [J].
GUANTI, G ;
BANFI, L ;
RIVA, R .
TETRAHEDRON-ASYMMETRY, 1994, 5 (01) :9-12
[5]   CHEMOENZYMATIC APPROACH TO THE AB RING-SYSTEM OF AKLAVINONE [J].
GUANTI, G ;
BANFI, L ;
BRUSCO, S ;
RIVA, R .
TETRAHEDRON LETTERS, 1993, 34 (52) :8549-8552
[6]   REGIOSELECTIVE SYNTHESIS OF 1,8-DIHYDROXYTETRALINS THROUGH A TANDEM REDUCTION INTRAMOLECULAR HYDROXYALKYLATION OF 4-(3-HYDROXYPHENYL)ALKANOATES [J].
GUANTI, G ;
BANFI, L ;
RIVA, R .
TETRAHEDRON, 1994, 50 (41) :11945-11966
[7]   ENZYME CATALYZED MONOHYDROLYSIS OF 2-ARYL-1,3-PROPANEDIOL DIACETATES - A STUDY OF STRUCTURAL EFFECTS OF THE ARYL MOIETY ON THE ENANTIOSELECTIVITY [J].
GUANTI, G ;
NARISANO, E ;
PODGORSKI, T ;
THEA, S ;
WILLIAMS, A .
TETRAHEDRON, 1990, 46 (20) :7081-7092
[8]  
GUANTI G, UNPUB TETRAHEDRON AS
[9]   PRACTICAL ASYMMETRIC-SYNTHESIS OF AKLAVINONE [J].
MCNAMARA, JM ;
KISHI, Y .
TETRAHEDRON, 1984, 40 (22) :4685-4691
[10]   ASYMMETRIC ADDITIONS TO CHIRAL NAPHTHALENES .4. AN ASYMMETRIC-SYNTHESIS OF THE AB-RING OF AKLAVINONE [J].
MEYERS, AI ;
HIGASHIYAMA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4592-4597