Synthesis of enynes related to neocarzinostatin using the new Pd/Ag catalyzed coupling reaction

被引:28
作者
Bertus, P [1 ]
Pale, P [1 ]
机构
[1] UNIV STRASBOURG 1,INST LE BEL,LAB SYNTH & REACT ORGAN,F-67000 STRASBOURG,FRANCE
关键词
D O I
10.1016/S0040-4039(97)10253-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Both E and Z isomers of 2-triflyloxymethylene cyclopentanone, 1 and 2 respectively, have been coupled with various functionalized acetylenes in the presence of the Pd/Ag set of catalysts. This method provides a rapid and stereoselective access to various E or Z 2-(alkynyl)methylene cyclopentanone derivatives, which are promising and versatile intermediates toward NCS-Chrom and analogs. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8193 / 8196
页数:4
相关论文
共 18 条
[1]   Silver salts as new catalyst for coupling reactions; Synthesis of epoxyenynes [J].
Bertus, P ;
Pale, P .
TETRAHEDRON LETTERS, 1996, 37 (12) :2019-2022
[2]  
COSSY J, 1987, TETRAHEDRON LETT, V51, P6039
[3]   THE STRUCTURE OF NEOCARZINOSTATIN CHROMOPHORE POSSESSING A NOVEL BICYCLO-[7,3,0]DODECADIYNE SYSTEM [J].
EDO, K ;
MIZUGAKI, M ;
KOIDE, Y ;
SETO, H ;
FURIHATA, K ;
OTAKE, N ;
ISHIDA, N .
TETRAHEDRON LETTERS, 1985, 26 (03) :331-334
[4]   MECHANISM OF NEOCARZINOSTATIN ACTION - ROLE OF DNA MICROSTRUCTURE IN DETERMINATION OF CHEMISTRY OF BISTRANDED OXIDATIVE DAMAGE [J].
GOLDBERG, IH .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :191-198
[5]   The chemistry of enediynes, enyne allenes and related compounds [J].
Grissom, JW ;
Gunawardena, GU ;
Klingberg, D ;
Huang, DH .
TETRAHEDRON, 1996, 52 (19) :6453-6518
[6]  
ISHIDA N, 1965, J ANTIBIOT, V18, P68
[7]   RATE AND MECHANISM OF OXIDATIVE ADDITION OF ARYL TRIFLATES TO ZEROVALENT PALLADIUM COMPLEXES - EVIDENCE FOR THE FORMATION OF CATIONIC (SIGMA-ARYL)PALLADIUM COMPLEXES [J].
JUTAND, A ;
MOSLEH, A .
ORGANOMETALLICS, 1995, 14 (04) :1810-1817
[8]   The enediyne and dienediyne based antitumour antibiotics. Methodology and strategies for total synthesis and construction of bioactive analogues .2. [J].
Lhermitte, H ;
Grierson, DS .
CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (02) :93-124
[9]   The enediyne and dienediyne based antitumour antibiotics. Methodology and strategies for total synthesis and construction of bioactive analogues .1. [J].
Lhermitte, H ;
Grierson, DS .
CONTEMPORARY ORGANIC SYNTHESIS, 1996, 3 (01) :41-63