SILVER-CATALYZED HETEROCYCLIZATION - FIRST TOTAL SYNTHESIS OF THE NATURALLY-OCCURRING CIS 2-HEXADECYL-3-HYDROXY-4-METHYLENE BUTYROLACTONE

被引：45
作者：
DALLA, V [1 ]
PALE, P [1 ]
机构：
[1] UFR SCI,CNRS,CHIM ORGAN PHYS LAB,F-51062 REIMS,FRANCE
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 21期
关键词：
SILVER-CATALYZED CYCLIZATION; GAMMA-ALKYLIDENE GAMMA-LACTONES; EXOCYCLIC ENOL LACTONES; 3-HYDROXY-4-METHYLENE BUTYROLACTONES; BETA-HYDROXY-GAMMA-ACETYLENIC ACIDS;
D O I：
10.1016/S0040-4039(00)73226-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title compound was obtained in 4 steps with an overall yield of 64% with the silver-catalyzed cyclization of the corresponding substituted beta- hydroxy-gamma- acetylenic acid as the key-step.
引用
收藏
页码：3525 / 3528
页数：4
相关论文
共 16 条
[1]   EFFICIENT SYNTHESIS OF "GAMMA-METHYLENE-GAMMA-BUTYROLACTONE (ALPHA-'-ANGELICALACTONE) - APPLICATION TO SYNTHESIS OF DEOXYOBTUSILACTONE AND DEOXYISOOBTUSILACTONE [J].
AMOS, RA ;
KATZENELLENBOGEN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :560-564
[2]   DIASTEREOSELECTIVE SYNTHESIS OF SPIROKETALS VIA RADICAL CYCLIZATION [J].
DALLA, V ;
PALE, P .
TETRAHEDRON LETTERS, 1992, 33 (51) :7857-7860
[3]  
DALLA V, 1990, DEA REPORT
[4]  
DIKSHIT DK, 1987, TETRAHEDRON LETT, V29, P3109
[5]   BASE-PROMOTED INTRAMOLECULAR CYCLIZATION OF BROMOACETYLENIC ALCOHOL DERIVATIVES [J].
GRANDJEAN, D ;
PALE, P ;
CHUCHE, J .
TETRAHEDRON LETTERS, 1992, 33 (34) :4905-4908
[6]  
GUANTI G, 1988, TETRAHEDRON, V44, P2685
[7]  
HEATHCOCK CH, 1985, ASYMMETRIC SYNTHESIS, V3, P115
[8]   SUBSTITUTED GAMMA-LACTONES WITH VICINAL HYDROGEN-ATOMS - CONFORMATIONAL STUDY BY MM2 CALCULATIONS AND COUPLING-CONSTANT ANALYSIS [J].
JAIME, C ;
SEGURA, C ;
DINARES, I ;
FONT, J .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) :154-158
[9]  
Larock R. C., 1991, COMPREHENSIVE ORGANI, V4, P269
[10]   A 2 STEP SYNTHESIS OF SPIROKETALS [J].
PALE, P ;
CHUCHE, J .
TETRAHEDRON LETTERS, 1988, 29 (24) :2947-2950
12