Towards new camptothecins.: Part 3:: Synthesis of 5-methoxycarbonyl camptothecin

被引：17

作者：

Brunin, T

Legentil, L

Hénichart, JP

Rigo, B

机构：

[1] Ecole Hautes Etud Ind, F-59046 Lille, France

[2] Univ Lille, Inst Chim Pharmaceut Albert Lespagnol, F-59006 Lille, France

来源：

TETRAHEDRON | 2006年 / 62卷 / 17期

关键词：

camptothecins; Mannich reaction; Bredereck's reagent;

D O I：

10.1016/j.tet.2006.02.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of two camptothecin analogs substituted by a carbonyl function on position 5 of cycle C was realized. New conditions were studied to obtain the E-lactone ring of these heterocycles. These compounds were obtained from the reaction of Bredereck's reagent with indolizines derived from pyroglutamic acid. This yielded dimethylaminovinyl groups whose oxidation by NaIO4 yielded ketones. The indolizinones obtained were reacted in Friedlander condition, to give the scaffold of the desired camptothecins. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3959 / 3968

页数：10

共 37 条

[1]

Ali MH, 1998, SYNTHESIS-STUTTGART, P1238

[2]

BORSCHE W, 1943, CHEM BER, V76, P1099

[3] Towards new camptothecins.: Part 2:: Synthesis of the ABCD ring scaffold substituted by a carboxyl group in the 5-position [J].