Chemo-, regio-, and enantioselective Pd-catalyzed allylic alkylation of indolocarbazole pro-aglycons

被引:91
作者
Trost, BM [1 ]
Krische, MJ [1 ]
Berl, V [1 ]
Grenzer, EM [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ol020046s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Monosubstituted isomerically pure indolopyrrolocarbazole precursors have been prepared via palladium-catalyzed asymmetric allylic alkylation methodology, employing both achiral cyclopentenyl electrophiles and chiral glycal derivatives. Chemoselective allylation of (bis)indole lactam pro-aglycon 3 allows access to N-distally substituted indolopyrrolocarbazole derivatives; glyoxamide precursor 14 provides entry into N-proximally substituted derivatives.
引用
收藏
页码:2005 / 2008
页数:4
相关论文
共 34 条
[1]  
Bergman J., 1988, STUDIES NATURAL PR A, V1, P3
[2]  
Eils S, 1999, SYNTHESIS-STUTTGART, P275
[3]   Cyclizations of unsymmetrical bis-1,2-(3-indolyl)ethanes: Synthesis of (-)-tjipanazole F1 [J].
Gilbert, EJ ;
Ziller, JW ;
VanVranken, DL .
TETRAHEDRON, 1997, 53 (48) :16553-16564
[4]  
GRIBBLE G, 1993, STUDIES NATURAL PROD, V123, P365
[5]   SYNTHESIS OF THE INDOLO[2,3-A]CARBAZOLE NATURAL-PRODUCTS STAUROSPORINONE AND ARCYRIAFLAVIN-B [J].
HUGHES, I ;
NOLAN, WP ;
RAPHAEL, RA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2475-2480
[6]   SYNTHESIS OF THE AROMATIC AND MONOSACCHARIDE MOIETIES OF STAUROSPORINE [J].
JOYCE, RP ;
GAINOR, JA ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1177-1185
[7]   Stereocontrolled total synthesis of (+)-K252a [J].
Kobayashi, Y ;
Fujimoto, T ;
Fukuyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6501-6502
[8]   REGIOSELECTIVE IMIDE REDUCTION - AN ISSUE IN THE TOTAL SYNTHESIS OF STAUROSPORINE [J].
LINK, JT ;
DANISHEFSKY, SJ .
TETRAHEDRON LETTERS, 1994, 35 (49) :9135-9138
[9]   Staurosporine and ent-staurosporine: The first total syntheses, prospects for a regioselective approach, and activity profiles [J].
Link, JT ;
Raghavan, S ;
Gallant, M ;
Danishefsky, SJ ;
Chou, TC ;
Ballas, LM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :2825-2842
[10]   EPOXIDES DERIVED FROM PYRANOSYL DIENES - UNUSUALLY STABLE GLYCOSYL DONORS [J].
LINK, JT ;
DANISHEFSKY, SJ ;
SCHULTE, G .
TETRAHEDRON LETTERS, 1994, 35 (49) :9131-9134