A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives

被引:66
作者
Leeuwenburgh, MA [1 ]
Kulker, C [1 ]
Duynstee, HI [1 ]
Overkleeft, HS [1 ]
van der Marel, GA [1 ]
van Boom, JH [1 ]
机构
[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands
关键词
D O I
10.1016/S0040-4020(99)00296-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8253 / 8262
页数:10
相关论文
共 23 条
[11]   Stereoselective synthesis of alpha-C-(alkynyl)-glycosides via ring-opening of alpha-1,2-anhydrosugars [J].
Leeuwenburgh, MA ;
Timmers, CM ;
vanderMarel, GA ;
vanBoom, JH ;
Mallet, JM ;
Sinay, PG .
TETRAHEDRON LETTERS, 1997, 38 (35) :6251-6254
[12]  
Leeuwenburgh MA, 1997, SYNLETT, P1263
[13]   ISOLATION AND STRUCTURE OF BREVETOXIN-B FROM THE RED TIDE DINOFLAGELLATE PTYCHODISCUS-BREVIS (GYMNODINIUM, BREVE) [J].
LIN, YY ;
RISK, M ;
RAY, SM ;
VANENGEN, D ;
CLARDY, J ;
GOLIK, J ;
JAMES, JC ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6773-6775
[14]   STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS [J].
MURATA, M ;
LEGRAND, AM ;
ISHIBASHI, Y ;
FUKUI, M ;
YASUMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4380-4386
[15]   USE OF METAL COMPLEXATION IN THE SYNTHESIS OF MEDIUM-RING ACETYLENIC LACTONES [J].
NAJDI, SD ;
OLMSTEAD, MM ;
SCHORE, NE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 431 (03) :335-358
[16]   CARBOHYDRATES IN ORGANIC-SYNTHESIS - SYNTHESIS OF 16-MEMBERED-RING MACROLIDE ANTIBIOTICS .5. TOTAL SYNTHESIS OF O-MYCINOSYLTYLONOLIDE - SYNTHESIS OF KEY INTERMEDIATES [J].
NICOLAOU, KC ;
PAVIA, MR ;
SEITZ, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) :2027-2029
[17]   Olefin metathesis in cyclic ether formation. Direct conversion of olefinic esters to cyclic enol ethers with Tebbe-type reagents [J].
Nicolaou, KC ;
Postema, MHD ;
Claiborne, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1565-1566
[18]   Convergent synthesis of the trans-fused 6-n-6-6 (n = 7-10) tetracyclic ether system based on a ring-closing metathesis reaction [J].
Oishi, T ;
Nagumo, Y ;
Hirama, M .
CHEMICAL COMMUNICATIONS, 1998, (09) :1041-1042
[19]   ENANTIOMERICALLY PURE INSECT PHEROMONES - THE CARBOHYDRATE SYNTHETIC APPROACH [J].
ROLLIN, P ;
KLAFFKE, W .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1991, 10 (02) :115-157
[20]   Synthesis and applications of RuCl2(=CHR')(PR(3))(2): The influence of the alkylidene moiety on metathesis activity [J].
Schwab, P ;
Grubbs, RH ;
Ziller, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) :100-110