Use of aldolases in the synthesis of non-carbohydrate natural products. Stereoselective synthesis of aspicilin C-3-C-9 fragment

被引:18
作者
Chenevert, R
Lavoie, M
Dasser, M
机构
[1] Départemem de Chimie, Fac. des Sci. et de Genie, Université Laval, Québec
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1997年 / 75卷 / 01期
关键词
aldolase; aspicilin; arabinose; synthesis;
D O I
10.1139/v97-010
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The C-3 - C-9 main fragment of aspicilin was prepared via a fructose 1,6-diphosphate aldolase reaction. The same fragment was also synthesized by chemical transformation starting from D-arabinose.
引用
收藏
页码:68 / 73
页数:6
相关论文
共 23 条
[11]   SUBSTANTIAL REFINEMENT OF THE PHOTOCHEMICAL-SYNTHESIS OF (+)-ASPICILIN [J].
QUINKERT, G ;
BECKER, H ;
DURNER, G .
TETRAHEDRON LETTERS, 1991, 32 (50) :7397-7400
[12]   SYNTHESIS OF (+)-ASPICILIN USING BUILDING-BLOCKS FROM RENEWABLE RESOURCES [J].
QUINKERT, G ;
FERNHOLZ, E ;
ECKES, P ;
NEUMANN, D ;
DURNER, G .
HELVETICA CHIMICA ACTA, 1989, 72 (08) :1753-1786
[13]   TOTAL SYNTHESIS OF THE ENANTIOMERICALLY PURE LICHEN MACROLIDE (+)-ASPICILIN [J].
QUINKERT, G ;
HEIM, N ;
GLENNEBERG, J ;
BILLHARDT, UM ;
AUTZE, V ;
BATS, JW ;
DURNER, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :362-364
[14]   STEREOSPECIFIC C-C-BOND FORMATION WITH RABBIT MUSCLE ALDOLASE - A CHEMOENZYMATIC SYNTHESIS OF (+)-EXO-BREVICOMIN [J].
SCHULTZ, M ;
WALDMANN, H ;
VOGT, W ;
KUNZ, H .
TETRAHEDRON LETTERS, 1990, 31 (06) :867-868
[15]  
SHIMAGAKI M, 1993, CHEM PHARM BULL, V41, P282
[16]   SHORT SYNTHESIS OF (+)-ASPICILIN VIA ASYMMETRIC HEXAHYDROXYLATION OF A TRIENE [J].
SINHA, SC ;
KEINAN, E .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) :949-951
[17]   ASYMMETRIC-SYNTHESIS OF THE MACROLIDE (-)-ASPICILIN [J].
SOLLADIE, G ;
FERNANDEZ, I ;
MAESTRO, C .
TETRAHEDRON-ASYMMETRY, 1991, 2 (08) :801-819
[18]   ENZYME-CATALYZED SYNTHESIS OF CARBOHYDRATES [J].
TOONE, EJ ;
SIMON, ES ;
BEDNARSKI, MD ;
WHITESIDES, GM .
TETRAHEDRON, 1989, 45 (17) :5365-5422
[19]  
TROST BM, 1991, COMPREHENSIVE ORGANI, V2
[20]   STEREOCONTROLLED TOTAL SYNTHESIS OF THE MACROCYCLIC LACTONE (-)-ASPICILIN [J].
WAANDERS, PP ;
THIJS, L ;
ZWANENBURG, B .
TETRAHEDRON LETTERS, 1987, 28 (21) :2409-2412