Stereoselective Synthesis of 3-Aryloctahydroindoles and Application in a Formal Synthesis of (−)-Pancracine

A stereoselective synthesis of 3-aryloctahydroindoles from enantiomerically enriched γ-nitroketones has been developed. Reduction of imines derived form the nitroketones provides the trans-fused octhaydroindole motif selectively. The cis-octahydroindole skeleton is accessible by an invertive cycliza...

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Bibliographic Details
Published in:Organic letters 2010-02, Vol.12 (3), p.556-559
Main Authors: Pansare, Sunil V, Lingampally, Rajinikanth, Kirby, Raie Lene
Format: Article
Language:English
Subjects:
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Stereoisomerism
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Summary:A stereoselective synthesis of 3-aryloctahydroindoles from enantiomerically enriched γ-nitroketones has been developed. Reduction of imines derived form the nitroketones provides the trans-fused octhaydroindole motif selectively. The cis-octahydroindole skeleton is accessible by an invertive cyclization strategy involving a diastereomerically pure nitromesylate intermediate. This approach was employed in the synthesis of an advanced intermediate to (−)-pancracine. The γ-nitroketone starting materials are readily available via an organocatalytic Michael reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902761a