A Fast Assembly of Pentacyclic Benz[f]indolo[2,3-a]quinolizidine Core by Tandem Intermolecular Formal Aza-[3 + 3] Cycloaddition/Pictet−Spengler Cyclization:  A Formal Synthesis of (±)-Tangutorine

We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-06, Vol.69 (13), p.4548-4550
Main Authors: Luo, Shengjun, Zhao, Jingrui, Zhai, Hongbin
Format: Article
Language:English
Subjects:
Carbolines - chemical synthesis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Preparations and properties
Quinolizines - chemical synthesis
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Summary:We have described a concise construction of the pentacyclic benz[f]indolo[2,3-a]quinolizidine intermediate 3 (with an overall yield of 54% for three steps), featuring a tandem intermolecular formal aza-[3 + 3] cycloaddition/Pictet−Spengler cyclization. The present work can be considered as a formal synthesis of β-carboline alkaloid (±)-tangutorine. Our strategy disclosed herein constitutes a new effective general synthetic approach toward the indoloquinolizidine family of alkaloids.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049459s