Further model studies related to fredericamycin A: Analogues in which ring C is expanded to six atoms, and an examination of the diastereoselectivity of radical spirocyclization

被引：24

作者：

Clive, DLJ

Kong, XL

Paul, CC

机构：

[1] Chemistry Department, University of Alberta, Edmonton

来源：

TETRAHEDRON | 1996年 / 52卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/0040-4020(96)00245-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The fredericamycin A analogues 5 and 23 were synthesized. A key step is the process of radical spirocyclization, and the diastereoselectivity of this reaction was studied with model compounds. In vitro tests showed that 23 was active against certain cell lines of colon and prostate cancer, while compound 5 was essentially inactive. (C) 1996 Elsevier Science Ltd.

引用

收藏

页码：6085 / 6116

页数：32

相关论文

共 17 条

[1]

BACK TG, 1993, SYNLETT, P699

[2] FUNCTIONAL-GROUP OXIDATION BY PENTAVALENT ORGANOBISMUTH REAGENTS [J].

BARTON, DHR ;

KITCHIN, JP ;

LESTER, DJ ;

MOTHERWELL, WB ;

PAPOULA, MTB .

TETRAHEDRON, 1981, 37 :73-79

[3] SYNTHESIS OF HETEROCYCLIC-COMPOUNDS RELATED TO FREDERICAMYCIN-A - THE CYCLOPENT[G]ISOQUINOLINE SYSTEM [J].

CLIVE, DLJ ;

SEDGEWORTH, J .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (02) :509-511

[4] TOTAL SYNTHESIS OF CRYSTALLINE (+/-)-FREDERICAMYCIN-A - USE OF RADICAL SPIROCYCLIZATION [J].

CLIVE, DLJ ;

TAO, Y ;

KHODABOCUS, A ;

WU, YJ ;

ANGOH, AG ;

BENNETT, SM ;

BODDY, CN ;

BORDELEAU, L ;

KELLNER, D ;

KLEINER, G ;

MIDDLETON, DS ;

NICHOLS, CJ ;

RICHARDSON, SR ;

VERNON, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (25) :11275-11286

[5] MODEL STUDIES RELATED TO THE SYNTHESIS OF FREDERICAMYCIN-A [J].

CLIVE, DLJ ;

KHODABOCUS, A ;

VERNON, PG ;

ANGOH, AG ;

BORDELEAU, L ;

MIDDLETON, DS ;

LOWE, C ;

KELLNER, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (06) :1433-1444

[6] RADICAL SPIROCYCLIZATION - SYNTHESIS OF AN APPROPRIATELY OXYGENATED SPIRO COMPOUND RELATED TO THE ANTITUMOR ANTIBIOTIC FREDERICAMYCIN-A [J].

CLIVE, DLJ ;

ANGOH, AG ;

BENNETT, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) :1339-1342

[7] USE OF RADICAL RING-OPENING FOR INTRODUCTION OF ALKYL AND SUBSTITUTED ALKYL-GROUPS WITH STEREOCHEMICAL CONTROL - A SYNTHETIC APPLICATION OF CYCLOPROPYLCARBINYL RADICALS [J].

CLIVE, DLJ ;

DAIGNEAULT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3801-3814

[8]

FIESER M, 1975, REAGENTS ORGANIC SYN, V5, P522

[9]

HUANG W, 1986, YOUJI HUAXUE, P376

[10] SYNTHESIS OF (+/-) FREDERICAMYCIN-A [J].

RAO, AVR ;

SINGH, AK ;

RAO, BV ;

REDDY, KM .

TETRAHEDRON LETTERS, 1993, 34 (16) :2665-2668