New Synthetic Method for Indole-2-carboxylate and Its Application to the Total Synthesis of Duocarmycin SA

The sequential coupling and cyclization reactions between aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivatives. On the other hand, the presence of an extra methyl propiolate...

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Bibliographic Details
Published in:Organic letters 2004-08, Vol.6 (17), p.2953-2956
Main Authors: Hiroya, Kou, Matsumoto, Shigemitsu, Sakamoto, Takao
Format: Article
Language:English
Subjects:
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Pyrroles - chemical synthesis
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Summary:The sequential coupling and cyclization reactions between aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivatives. On the other hand, the presence of an extra methyl propiolate and Pd(PPh3)4 were required to provide an efficient catalytic system for the cyclization reactions. This reaction was used for the total synthesis of duocarmycin SA.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0489548