Intramolecular Formal Aza-[3 + 3] Cycloaddition Approach to Indoloquinolizidine Alkaloids. A Stereoselective Total Synthesis of (±)-Tangutorine

A 19-step stereoselective total synthesis of (±)-tangutorine is described here. The total synthesis features an intramolecular aza-[3 + 3] formal cycloaddition strategy and also a Heck coupling for constructing the C2−C3 bond. This work provides a novel approach toward the indoloquinolizidine family...

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Bibliographic Details
Published in:Organic letters 2003-11, Vol.5 (24), p.4709-4712
Main Authors: Luo, Shengjun, Zificsak, Craig A, Hsung, Richard P
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Aza Compounds - chemistry
Carbolines - chemical synthesis
Carbolines - chemistry
Indolequinones - chemistry
Molecular Structure
Quinolizines - chemical synthesis
Quinolizines - chemistry
Stereoisomerism
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Summary:A 19-step stereoselective total synthesis of (±)-tangutorine is described here. The total synthesis features an intramolecular aza-[3 + 3] formal cycloaddition strategy and also a Heck coupling for constructing the C2−C3 bond. This work provides a novel approach toward the indoloquinolizidine family of alkaloids.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol030114q