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.

引用

页码：1043 / 1046

页数：4

共 20 条

[1] AOKI K, 1993, CHEM PHARM BULL, V41, P994
[2] GADAIN, A LIGNAN FROM JATROPHA-GOSSYPIFOLIA
BANERJI, J
DAS, B
CHATTERJEE, A
SHOOLERY, JN
[J]. PHYTOCHEMISTRY, 1984, 23 (10) : 2323 - 2327
[3] CHEMISTRY AND SYNTHESIS OF LIGNAN(-)-CUBEBIN
BATTERBEE, JE
BURDEN, RS
CROMBIE, L
WHITING, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18): : 2470 - +
[4] ASYMMETRIC DEPROTONATION OF PROCHIRAL KETONES USING CHIRAL LITHIUM AMIDE BASES
CAIN, CM
COUSINS, RPC
COUMBARIDES, G
SIMPKINS, NS
[J]. TETRAHEDRON, 1990, 46 (02) : 523 - 544
[5] ASYMMETRIC-SYNTHESIS USING HOMOCHIRAL LITHIUM AMIDE BASES
COX, PJ
SIMPKINS, NS
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (01) : 1 - 26
[6] CHEMISTRY OF THE ORDER CUPRESSALES .58. PHENOLIC AND TERPENOID HEARTWOOD CONSTITUENTS OF LIBOCEDRUS-YATEENSIS
ERDTMAN, H
HARMATHA, J
[J]. PHYTOCHEMISTRY, 1979, 18 (09) : 1495 - 1500
[7] SHORT REGIOSELECTIVE SYNTHESIS OF (+/-)-ALPHA-CUPARENONE VIA 3-CARBON ANNELATION
GREENE, AE
LANSARD, JP
LUCHE, JL
PETRIER, C
[J]. 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
HONDA, T
KIMURA, N
TSUBUKI, M
[J]. 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
ISHIBASHI, H
ITO, K
HIRANO, T
TABUCHI, M
IKEDA, M
[J]. TETRAHEDRON, 1993, 49 (20) : 4173 - 4182
[10] ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS
KOCH, SSC
CHAMBERLIN, AR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) : 2725 - 2737

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