CHIRAL SYNTHESIS OF LIGNAN LACTONES, (-)-HINOKININ, (-)-DEOXYPODORHIZONE, (-)-ISOHIBALACTONE AND (-)-SAVININ BY MEANS OF ENANTIOSELECTIVE DEPROTONATION STRATEGY

被引：49

作者：

HONDA, T ^{[1
]}

KIMURA, N ^{[1
]}

SATO, S ^{[1
]}

KATO, D ^{[1
]}

TOMINAGA, H ^{[1
]}

机构：

[1] JPS PHARMACEUT CO LTD, HAGA, TOCHIGI 32133, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 08期

关键词：

D O I：

10.1039/p19940001043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral synthesis of lignan lactones, (-)-hinokinin, (-)-deoxypodorhizone, (-)-isohibalactone and (-)-savinin, has been achieved by employing an enantioselective deprotonation of 3-(3,4-methylene-dioxybenzyl)cyclobutanone with lithium (S.S')-alpha,alpha'-dimethyldibenzylamide, as a key step.

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页码：1043 / 1046

页数：4

相关论文

共 20 条

[1]

AOKI K, 1993, CHEM PHARM BULL, V41, P994

[2] GADAIN, A LIGNAN FROM JATROPHA-GOSSYPIFOLIA [J].

BANERJI, J ;

DAS, B ;

CHATTERJEE, A ;

SHOOLERY, JN .

PHYTOCHEMISTRY, 1984, 23 (10) :2323-2327

[3] CHEMISTRY AND SYNTHESIS OF LIGNAN(-)-CUBEBIN [J].

BATTERBEE, JE ;

BURDEN, RS ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2470-+

[4] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES [J].

CAIN, CM ;

COUSINS, RPC ;

COUMBARIDES, G ;

SIMPKINS, NS .

TETRAHEDRON, 1990, 46 (02) :523-544

[5] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES [J].

COX, PJ ;

SIMPKINS, NS .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :1-26

[6] CHEMISTRY OF THE ORDER CUPRESSALES .58. PHENOLIC AND TERPENOID HEARTWOOD CONSTITUENTS OF LIBOCEDRUS-YATEENSIS [J].

ERDTMAN, H ;

HARMATHA, J .

PHYTOCHEMISTRY, 1979, 18 (09) :1495-1500

[7] SHORT REGIOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-CUPARENONE VIA 3-CARBON ANNELATION [J].

GREENE, AE ;

LANSARD, JP ;

LUCHE, JL ;

PETRIER, C .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4763-4764

[8] CHIRAL SYNTHESIS OF 3-SUBSTITUTED AND 3,3-DISUBSTITUTED GAMMA-BUTYROLACTONES BY ENANTIOSELECTIVE DEPROTONATION STRATEGY [J].

HONDA, T ;

KIMURA, N ;

TSUBUKI, M .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1475-1478

[9] SYNTHESIS OF PODOPHYLLOTOXIN DERIVATIVES BY MEANS OF TRIBUTYLTIN HYDRIDE-MEDIATED OR PALLADIUM-MEDIATED CYCLIZATION OF ALPHA-BENZYLIDENE-BETA-(O-BROMOBENZYL)-GAMMA-LACTONES [J].

ISHIBASHI, H ;

ITO, K ;

HIRANO, T ;

TABUCHI, M ;

IKEDA, M .

TETRAHEDRON, 1993, 49 (20) :4173-4182

[10] ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS [J].

KOCH, SSC ;

CHAMBERLIN, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) :2725-2737