STEREOSELECTIVE SYNTHESES OF DISUBSTITUTED, TRISUBSTITUTED AND TETRASUBSTITUTED ENEDIYNES FROM ENYNYL IODIDES VIA PD-CATALYZED COUPLING REACTIONS

被引:32
作者
STRACKER, EC [1 ]
ZWEIFEL, G [1 ]
机构
[1] UNIV CALIF DAVIS,DEPT CHEM,DAVIS,CA 95616
关键词
D O I
10.1016/S0040-4039(00)92698-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium catalyzed cross-coupling of iodoenynes derived from mono(stannyl)enynes with alkynyl zinc reagents affords isomerically pure conjugated di-, tri- and tetrasubstituted (Z)-enediynes and trisubstituted cross-conjugated enediynes in high yields.
引用
收藏
页码:3329 / 3332
页数:4
相关论文
共 29 条
[1]   A CONCISE ROUTE TO THE CALICHEAMICIN-ESPERAMICIN SERIES - THE CRYSTAL-STRUCTURE OF A CORE SUBUNIT [J].
DANISHEFSKY, SJ ;
MANTLO, NB ;
YAMASHITA, DS ;
SCHULTE, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6890-6891
[2]   ESPERAMICINS, A NOVEL CLASS OF POTENT ANTITUMOR ANTIBIOTICS .2. STRUCTURE OF ESPERAMICIN-X [J].
GOLIK, J ;
CLARDY, 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) :3461-3462
[3]   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
[4]   EXPERIMENTAL MODELING OF THE PRIMING MECHANISM OF THE CALICHEAMICIN ESPERAMICIN ANTIBIOTICS - ACTUATION BY THE ADDITION OF INTRAMOLECULAR NUCLEOPHILES TO THE BRIDGEHEAD DOUBLE-BOND [J].
HASELTINE, JN ;
DANISHEFSKY, SJ ;
SCHULTE, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7638-7640
[5]   MODEL OF THE INTERACTIONS OF CALICHEMICIN-GAMMA-1 WITH A DNA FRAGMENT FROM PBR322 [J].
HAWLEY, RC ;
KIESSLING, LL ;
SCHREIBER, SL .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (04) :1105-1109
[6]   MECHANISM AND BASE SPECIFICITY OF DNA BREAKAGE IN INTACT-CELLS BY NEOCARZINOSTATIN [J].
KAPPEN, LS ;
ELLENBERGER, TE ;
GOLDBERG, IH .
BIOCHEMISTRY, 1987, 26 (02) :384-390
[7]   SYNTHESIS OF A CALICHEAMICIN DEOXYAGLYCONE MODEL BY AN INTRAMOLECULAR ACETYLIDE CYCLIZATION [J].
KENDE, AS ;
SMITH, CA .
TETRAHEDRON LETTERS, 1988, 29 (34) :4217-4220
[8]   DYNEMICIN A, A NOVEL ANTIBIOTIC WITH THE ANTHRAQUINONE AND 1,5-DIYN-3-ENE SUBUNIT [J].
KONISHI, M ;
OHKUMA, H ;
MATSUMOTO, K ;
TSUNO, T ;
KAMEI, H ;
MIYAKI, T ;
OKI, T ;
KAWAGUCHI, H ;
VANDUYNE, GD ;
CLARDY, J .
JOURNAL OF ANTIBIOTICS, 1989, 42 (09) :1449-1452
[9]   CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .1. CHEMISTRY AND PARTIAL STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].
LEE, MD ;
DUNNE, TS ;
SIEGEL, MM ;
CHANG, CC ;
MORTON, GO ;
BORDERS, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3464-3466
[10]   CALICHEMICINS, A NOVEL FAMILY OF ANTITUMOR ANTIBIOTICS .2. CHEMISTRY AND STRUCTURE OF CALICHEMICIN-GAMMA-1 [J].
LEE, MD ;
DUNNE, TS ;
CHANG, CC ;
ELLESTAD, GA ;
SIEGEL, MM ;
MORTON, GO ;
MCGAHREN, WJ ;
BORDERS, DB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (11) :3466-3468