A NOVEL-APPROACH TO THE SYNTHESIS OF ENEDIYNES

被引:61
作者
MAGRIOTIS, PA
SCOTT, ME
KIM, KD
机构
[1] Department of Chemistry, West Virginia University, Morgantown
关键词
STANNYLCUPRATION; 1-PHENYLTHIO-1-ALKYNES; VINYLCOPPER-ZINC INTERMEDIATES; STANNYL ENYNES; ENEDIYNES;
D O I
10.1016/0040-4039(91)80759-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of enediynes is described based on stannylcupration of acetylene and certain activated alkynes, in situ reaction with 1-halo-1-alkynes, iododestannylation, and Pd(0)-catalyzed coupling with terminal alkynes.
引用
收藏
页码:6085 / 6088
页数:4
相关论文
共 38 条
[1]   ALKENYL COPPER REAGENTS .18. CARBOCUPRATION OF ACETYLENIC ACETALS AND KETALS SYNTHESIS OF MANICONE, GERANIAL AND 2,4 (E,Z)-DIENALS [J].
ALEXAKIS, A ;
COMMERCON, A ;
COULENTIANOS, C ;
NORMANT, JF .
TETRAHEDRON, 1984, 40 (04) :715-731
[2]   STEREOSPECIFIC SYNTHESIS OF CONJUGATED ENYNES FROM ALKENYLDIALKYLBORANES VIA ALKENYLCOPPER INTERMEDIATES [J].
BROWN, HC ;
MOLANDER, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (03) :645-647
[3]   SUBSTITUTION OF 1-HALO-1-ALKYNES BY ORGANOMETALLIC DERIVATIVES OF COPPER - SYNTHESIS OF NEW CLASS OF SYNTHONS - APPLICATION TO SYNTHESIS OF BOMBYKOL [J].
COMMERCON, A ;
NORMANT, JF ;
VILLIERAS, J .
TETRAHEDRON, 1980, 36 (09) :1215-1221
[4]  
CROMBIE L, 1979, J CHEM SOC P1, V9, P2136
[5]   GENERATION AND CARBONYL ADDITION-REACTIONS OF Z-DILITHIOHEX-3-ENE-1,5-DIYNE [J].
DANISHEFSKY, SJ ;
YAMASHITA, DS ;
MANTLO, NB .
TETRAHEDRON LETTERS, 1988, 29 (37) :4681-4684
[6]   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
[7]   ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .3. STRUCTURES OF ESPERAMICINS-A1, ESPERAMICIN-A2, AND ESPERAMICIN-A1B [J].
GOLIK, J ;
DUBAY, G ;
GROENEWOLD, G ;
KAWAGUCHI, H ;
KONISHI, M ;
KRISHNAN, B ;
OHKUMA, H ;
SAITOH, K ;
DOYLE, TW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3462-3464
[8]   TOTAL SYNTHESIS OF CALICHEAMICINONE - NEW ARRANGEMENTS FOR ACTUATION OF THE REDUCTIVE CYCLOAROMATIZATION OF AGLYCON CONGENERS [J].
HASELTINE, JN ;
CABAL, MP ;
MANTLO, NB ;
IWASAWA, N ;
YAMASHITA, DS ;
COLEMAN, RS ;
DANISHEFSKY, SJ ;
SCHULTE, GK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3850-3866
[9]   SPECTROSCOPIC AND CHEMICAL EVIDENCE FOR THE REVERSIBLE FORMATION OF VINYLCOPPER INTERMEDIATES IN THE STANNYLCUPRATION OF TERMINAL ALKYNES [J].
HUTZINGER, MW ;
SINGER, RD ;
OEHLSCHLAGER, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (25) :9397-9398
[10]   HIGHLY GENERAL STEREO-SELECTIVE, REGIO-SELECTIVE, AND CHEMO-SELECTIVE SYNTHESIS OF TERMINAL AND INTERNAL CONJUGATED ENYNES BY PD-CATALYSED REACTION OF ALKYNYLZINC REAGENTS WITH ALKENYL HALIDES [J].
KING, AO ;
OKUKADO, N ;
NEGISHI, EI .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (19) :683-684