Synthesis of thienodolin

被引：32

作者：

Engqvist, R

Javaid, A

Bergman, J

机构：

[1] Karolinska Inst, Novum, CNT, Dept Biosci,Unit Organ Chem, S-14157 Huddinge, Sweden

[2] Sodertorn Univ Coll, S-14104 Huddinge, Sweden

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 12期

关键词：

alkaloid; total synthesis; indoles;

D O I：

10.1002/ejoc.200400073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a total synthesis of the alkaloid thienodolin (1a), as well as its 5-chloro isomer 1b and its unsubstituted analogue 1c, in three steps from the corresponding oxindoles Ba-c. The preparation was achieved through an initial Vilsmeier-Haack-Arnold reaction (chloro-formylation) followed by protection at the indole nitrogen, creation of the fused thiophene ring by nucleophilic substitution at the 2-position and an intramolecular cyclization using mercaptoacetamide. This gave 1a, 1b and 1c in total yields of 42%, 35% and 37%, respectively. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：2589 / 2592

页数：4

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