Rapid Total Synthesis of (±)Trigonoliimine A via a Strecker/Houben–Hoesch Sequence

A novel synthetic route to the hexacyclic system of trigonoliimine A was accomplished in four steps from N-phthaloyl 6-OMe-tryptamine. Key reactions include a three-component Strecker-type reaction to fashion the two C–N bonds in the D ring and a subsequent Houben–Hoesch type cyclization to deliver...

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Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (3), p.528-530
Main Authors: Zhao, Bing, Hao, Xiao-Yan, Zhang, Jian-Xin, Liu, Sheng, Hao, Xiao-Jiang
Format: Article
Language:English
Subjects:
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Stereoisomerism
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Summary:A novel synthetic route to the hexacyclic system of trigonoliimine A was accomplished in four steps from N-phthaloyl 6-OMe-tryptamine. Key reactions include a three-component Strecker-type reaction to fashion the two C–N bonds in the D ring and a subsequent Houben–Hoesch type cyclization to deliver the characteristic seven-membered C ring.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303344d