Enantioselective synthesis of benzylbutyrolactones from 5-hydroxyfuran-2(5H)-one.: New chiral synthons for dibenzylbutyrolactone lignans by a chemoenzymatic route

被引：26

作者：

Brinksma, J ^{[1
]}

van der Deen, H ^{[1
]}

van Oeveren, A ^{[1
]}

Feringa, BL ^{[1
]}

机构：

[1] Univ Groningen, Organ Chem Lab, NL-9747 AG Groningen, Netherlands

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 24期

关键词：

D O I：

10.1039/a805777j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemoenzymatic method is described for the asymmetric synthesis of benzylbutyrolactones. (R)-5-Acetoxyfuran-2(5H)-one (12) was obtained with ee >99% in a multigram scale catalytic esterification using immobilized lipase PS. The addition of lithiated dithianes to chiral synthon 12 was followed by an effective multistep reduction to produce enantiomerically pure benzylbutyrolactones.

引用

页码：4159 / 4163

页数：5

共 25 条

[1] AYRES DC, 1990, LIGNANS
[2] Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones
Bode, JW
Doyle, MP
Protopopova, MN
Zhou, QL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9146 - 9155
[3] RESOLUTION OF (+/-)-TRANS-SOBREROL BY LIPASE PS-CATALYZED TRANSESTERIFICATION AND EFFECTS OF ORGANIC-SOLVENTS ON ENANTIOSELECTIVITY
BOVARA, R
CARREA, G
FERRARA, L
RIVA, S
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (09) : 931 - 938
[4] (R)-(+)-BETA-VERATRYL-GAMMA-BUTYROLACTONE, A NEW KEY-INTERMEDIATE FOR THE ASYMMETRIC-SYNTHESIS OF VARIOUS LIGNANS
BROWN, E
DAUGAN, A
[J]. TETRAHEDRON LETTERS, 1986, 27 (32) : 3719 - 3722
[5] FERINGA BL, 1987, RECL TRAV CHIM PAY B, V106, P481
[6] CHARACTERIZATION OF ANTI-HIV LIGNANS FROM LARREA-TRIDENTATA
GNABRE, J
HUANG, RCC
BATES, RB
BURNS, JJ
CALDERA, S
MALCOMSON, ME
MCCLURE, KJ
[J]. TETRAHEDRON, 1995, 51 (45) : 12203 - 12210
[7] Haworth J.L., 1936, ANN REPORTS PROGR CH, V33, P266, DOI DOI 10.1039/AR9363300228
[8] AN EFFICIENT ENANTIOSELECTIVE TOTAL SYNTHESIS OF ANTITUMOR LIGNANS - SYNTHESIS OF ENANTIOMERICALLY PURE 4-HYDROXYALKANENITRILES VIA AN ENZYMATIC-REACTION
ITOH, T
CHIKA, J
TAKAGI, Y
NISHIYAMA, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) : 5717 - 5723
[9] JANSEN JFG, 1991, THESIS U GRONINGEN
[10] ASYMMETRIC 1,4-ADDITIONS TO GAMMA-MENTHYLOXYBUTENOLIDES .4. 2 ENANTIOSELECTIVE SYNTHESES OF 2-METHYL-1,4-BUTANEDIOL
JANSEN, JFGA
FERINGA, BL
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (09) : 1367 - 1376

← 1 2 3 →