The Dimerization of Precocene I

In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium tribromide (PTT) blocks its oligomerization givin...

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Bibliographic Details
Published in:Natural product communications 2017-05, Vol.12 (5), p.691-694
Main Authors: Fraga, Braulio M., Cabrera, Inmaculada
Format: Article
Language:English
Subjects:
Benzopyrans - chemistry
Dimerization
Molecular Structure
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Summary:In an earlier work we reported that treatment of precocene I with Brönsted and Lewis acids produces its oligomerization, giving dimers, trimers, tetramers, etc. Now, in this article we show that bromination of precocene I with phenyltrimethylammonium tribromide (PTT) blocks its oligomerization giving a dibromo-dimer, which was reduced with tri-n-butyl tin hydride affording the same dimer obtained in the reactions with acid, thus avoiding the oligomerization. Additionally, the oxidations of precocene I with Jones reagent afforded the corresponding 3-hydroxy-4-chromanone, 3,4-chromandione, 3,4-diacid, and two dimers.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1701200512