A new diastereoselective approach to simplified Dynemicin analogues

被引:14
作者
Guanti, G
Riva, R
机构
[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy
[2] Univ Genoa, CNR, CSCCA, I-16146 Genoa, Italy
关键词
D O I
10.1039/b002031l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereoselective synthesis of new simplified Dynemicin analogues is reported: key steps of the sequence are the regio- and diastereo-selective functionalization of a quinoline nucleus, bearing a substituent with a stereogenic centre, and the formation of the 10-membered cyclic enediyne system by Pd-catalyzed Stille-like reaction.
引用
收藏
页码:1171 / 1172
页数:2
相关论文
共 23 条
[1]  
Banfi L, 2000, EUR J ORG CHEM, V2000, P939
[2]   Lipase catalyzed asymmetrization of quinolyl substituted 1,3-propanediols [J].
Banfi, L ;
Guanti, G ;
Mugnoli, A ;
Riva, R .
TETRAHEDRON-ASYMMETRY, 1998, 9 (14) :2481-2492
[3]   Rational design, synthesis, and reactivity of lactendiynes, a new class of cyclic enediynes ortho-fused with the beta-lactam ring [J].
Banfi, L ;
Basso, A ;
Guanti, G .
TETRAHEDRON, 1997, 53 (09) :3249-3268
[4]   Synthesis of (±)-calicheamicinone by two methods [J].
Clive, DLJ ;
Bo, YX ;
Tao, Y ;
Daigneault, S ;
Wu, YJ ;
Meignan, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (40) :10332-10349
[5]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[6]   Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol [J].
Guanti, G ;
Perrozzi, S ;
Riva, R .
TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3923-3927
[7]   PROTECTING GROUP CONTROLLED DIASTEREOSELECTIVE REDUCTION OF DIPROTECTED ALPHA,ALPHA-BIS(HYDROXYMETHYL)KETONES DERIVED FROM THYM-ASTERISK, USING THE DIBALH MGBR2 SYSTEM [J].
GUANTI, G ;
BANFI, L ;
RIVA, R ;
ZANNETTI, MT .
TETRAHEDRON LETTERS, 1993, 34 (34) :5483-5486
[8]   A MILD AND EFFICIENT ROUTE TO THE PHARMACOPHORE OF THE ENEDIYNE ANTITUMOR AGENTS - (Z)-1,6-[BIS (TRIMETHYLSILYL)]-HEX-3-ENE-1,5-DIYNE VIA A NOVEL CARBENOID COUPLING REACTION [J].
HUBER, RS ;
JONES, GB .
TETRAHEDRON LETTERS, 1994, 35 (17) :2655-2658
[9]  
Maier ME, 1999, EUR J ORG CHEM, V1999, P1
[10]   Effects of propargylic substitution and annelation on the cycloaromatization of a bicyclo[7.3.1] enediyne [J].
Moss, DK ;
Spence, JD ;
Nantz, MH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4339-4343