SYNTHESIS OF A CYCLITOL VIA A TANDEM ENZYMATIC ALDOL - INTRAMOLECULAR HORNER-WADSWORTH-EMMONS REACTION

被引:21
作者
GIJSEN, HJM [1 ]
WONG, CH [1 ]
机构
[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/0040-4039(95)01483-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol condensation between a phosphonate aldehyde and dihydroxyacetone phosphate catalyzed by fructose 1,6-diphosphate aldolase (EC 4.1.2.13) gives a product which in situ cyclizes via an intramolecular Horner-Wadsworth-Emmans (HWE) olefination to afford a polyhydroxylated cyclopentene. In this one-pot reaction, the HWE reaction takes place in aqueous solution at slightly acidic (pH 6.1-6.8) conditions.
引用
收藏
页码:7057 / 7060
页数:4
相关论文
共 18 条
[1]  
AIYAGI T, 1989, J ANTIBIOT, V42, P883
[2]   CYCLOALKENES BY INTRAMOLECULAR WITTIG REACTION [J].
BECKER, KB .
TETRAHEDRON, 1980, 36 (12) :1717-1745
[3]  
BERGMEYER HU, 1984, METHOD ENZYMAT AN, V11, P146
[4]   SYNTHESIS OF NITROCYCLITOLS BASED ON ENZYMATIC ALDOL REACTION AND INTRAMOLECULAR NITROALDOL REACTION [J].
CHOU, WC ;
FOTSCH, C ;
WONG, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2916-2917
[5]   ACTIVE-SITE LABELING OF TRIOSE PHOSPHATE ISOMERASE - REACTION OF BROMOHYDROXYACETONE PHOSPHATE WITH A UNIQUE GLUTAMIC-ACID RESIDUE AND MIGRATION OF LABEL TO TYROSINE [J].
DELAMARE, S ;
KNOWLES, JR ;
COULSON, AFW ;
PRIDDLE, JD ;
OFFORD, RE .
BIOCHEMICAL JOURNAL, 1972, 129 (02) :321-&
[6]  
DINCAN E, 1975, SYNTHESIS-STUTTGART, P516
[7]  
DRAUZ K, 1995, CATALYSIS ORGANIC SY
[8]   SYNTHESIS OF 1S,2R,3S,4R,5R-METHYL[2,3,4-TRIHYDROXY-5-(HYDROXYMETHYL)CYCLOPENTYL]AMINE - A POTENT ALPHA-MANNOSIDASE INHIBITOR [J].
FARR, RA ;
PEET, NP ;
KANG, MS .
TETRAHEDRON LETTERS, 1990, 31 (49) :7109-7112
[9]   THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES [J].
FERRIER, RJ ;
MIDDLETON, S .
CHEMICAL REVIEWS, 1993, 93 (08) :2779-2831
[10]   SYNTHESIS OF VALIOLAMINE AND ITS N-SUBSTITUTED DERIVATIVES AO-128, VALIDOXYLAMINE-G, AND VALIDAMYCIN-G VIA BRANCHED-CHAIN INOSOSE DERIVATIVES [J].
FUKASE, H ;
HORII, S .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) :3651-3658