Synthesis of Pentacyclic 13-Azadibenzo[a,d e]anthracenes via Anionic Cascade Ring Closure

Bromine−lithium exchange using tert-butyllithium at −78 °C initiates a cascade process whereby either xanthone derivatives or pentacyclic 13-azadibenzo[a,de]anthracenes are produced in high yields. The reaction proceeds via a sequential intramolecular trapping of organolithium intermediates.

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Bibliographic Details
Published in:Journal of organic chemistry 2003-05, Vol.68 (10), p.4091-4092
Main Authors: Kristensen, Jesper L, Vedsø, Per, Begtrup, Mikael
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Steroids
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Description
Summary:Bromine−lithium exchange using tert-butyllithium at −78 °C initiates a cascade process whereby either xanthone derivatives or pentacyclic 13-azadibenzo[a,de]anthracenes are produced in high yields. The reaction proceeds via a sequential intramolecular trapping of organolithium intermediates.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0300340