Affiliation:
1. Instituto de Productos Naturales y Agrobiología, C.S.I.C., Avda. Astrofísico F. Sánchez 3, 38206-La Laguna, Tenerife, Canary Islands, Spain
2. Instituto Universitario de Bioorgánica “Antonio González”, Universidad de La Laguna, Tenerife, Spain
Abstract
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.
Subject
Complementary and alternative medicine,Plant Science,Drug Discovery,Pharmacology,General Medicine