γ-Methyl-substituted-γ-butyrolactones:: solid-phase synthesis employing a cyclisation-cleavage strategy

被引:48
作者
Gouault, N [1 ]
Cupif, JF [1 ]
Sauleau, A [1 ]
David, M [1 ]
机构
[1] Fac Pharm, Lab Chim Pharmaceut, UPRES Pharmacochim Mol Synth & Subst Nat, F-35043 Rennes, France
关键词
D O I
10.1016/S0040-4039(00)00921-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The solid-phase synthesis of several gamma-methyl-substituted-gamma-butyrolactones using a cyclisation-cleavage reaction is reported. Chemical modifications of polymer-bound azido (2a) and iodo alcohols (2b) were realised in order to introduce additional diversity onto the lactone structure. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7293 / 7297
页数:5
相关论文
共 12 条
[1]  
BASTIDE J, 1973, B SOC CHIM FR II-CH, P2555
[2]   SYNTHESIS OF CHIRAL FUNCTIONALIZED TRANS-BETA-ISOPROPENYL-GAMMA-(HYDROXYMETHYL)-GAMMA-BUTYROLACTONES [J].
CAINE, D ;
VENKATARAMU, SD ;
KOIS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2960-2963
[3]   LANTHANIDE(III) TRIFLUOROMETHANESULFONATES AS EXTRAORDINARILY EFFECTIVE NEW CATALYSTS FOR THE AMINOLYSIS OF 1,2-EPOXIDES [J].
CHINI, M ;
CROTTI, P ;
FAVERO, L ;
MACCHIA, F ;
PINESCHI, M .
TETRAHEDRON LETTERS, 1994, 35 (03) :433-436
[4]   Synthesis of (+)- and (-)-phaseolinic acid by combination of enzymatic hydrolysis and chemical transformations with revision of the absolute configuration of the natural product [J].
Drioli, S ;
Felluga, F ;
Forzato, C ;
Nitti, P ;
Pitacco, G ;
Valentin, E .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07) :2385-2388
[5]   SYNTHESIS OF 3 JASMIN CONSTITUENTS VIA A CENTRAL INTERMEDIATE [J].
DUBS, P ;
STUSSI, R .
HELVETICA CHIMICA ACTA, 1978, 61 (03) :990-997
[6]  
Gouault N., 1999, Pharmacy and Pharmacology Communications, V5, P159
[7]   2-SILOXY-SUBSTITUTED METHYL CYCLOPROPANECARBOXYLATES AS BUILDING-BLOCKS IN SYNTHESIS - EFFICIENT ONE-POT CONVERSION TO GAMMA-BUTYROLACTONES [J].
GRIMM, EL ;
REISSIG, HU .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :242-244
[8]  
LeHetet C, 1997, TETRAHEDRON LETT, V38, P5153
[9]   SYNTHESIS OF OPTICALLY-ACTIVE PHEROMONES [J].
MORI, K .
TETRAHEDRON, 1989, 45 (11) :3233-3298
[10]  
Mousseron M., 1952, B SOC CHIM FR, P757