Catalytic Selective Cyclizations of Aminocyclopropanes: Formal Synthesis of Aspidospermidine and Total Synthesis of Goniomitine

被引：143

作者：

De Simone, Filippo ^{[1
]}

Gertsch, Juerg ^{[2
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, EPFL SB ISIC LCSO, CH-1015 Lausanne, Switzerland

[2] Inst Biochem & Mol Med, CH-3012 Bern, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 33期

关键词：

alkaloids; antitumor agents; cyclization; heterocycles; regioselectivity; ARYL CYCLOPROPYL KETONES; NAZAROV CYCLIZATION; DL-ASPIDOSPERMIDINE; ORGANIC-SYNTHESIS; ALKALOIDS; INDOLE; (+/-)-ASPIDOSPERMIDINE; (+)-ASPIDOSPERMIDINE; QUEBRACHAMINE; VINBLASTINE;

D O I：

10.1002/anie.201001853

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Mild control: Selective cyclization of aminocyclopropanes at either the N1 or C3 position of an indole ring was achieved by tuning the reaction conditions (see scheme). This strategy was applied to the formal synthesis of aspidospermidine and the total synthesis of goniomitine, which demonstrated significant cytotoxicity against several tumor cell lines (IC50 = 150-400 nM). Cbz = benzyloxycarbonyl, Ts = 4-toluenesulfonyl. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5767 / 5770

页数：4

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