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RESEARCH ARTICLE
Contents Vol 64(5)

The Heck Reaction of Protected Hydroxychromones: on route to Natural Products

Attila Vasas A , Tamás Patonay A C , Krisztina Kónya A , Artur M. S. Silva B and José A. S. Cavaleiro B
+ Author Affiliations
- Author Affiliations

A Department of Organic Chemistry, University of Debrecen, Egyetem tér 1, 4032 Debrecen, Hungary.

B Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal.

C Corresponding author. Email: patonay.tamas@science.unideb.hu

Australian Journal of Chemistry 64(5) 647-657 https://doi.org/10.1071/CH10296
Submitted: 9 August 2010  Accepted: 8 March 2011   Published: 30 May 2011

Abstract

The Heck reaction has been successfully extended to the bromochromones with an adjacent protected phenolic hydroxy group which offers a new methodology to various naturally occurring derivatives including tricyclic O-heterocycles. Phosphine-free coupling conditions are found to be effective. Surprisingly, the methoxymethyl protecting group is unstable in several cases but benzyl proved to be an ideal protecting group which could be selectively cleaved by boron trihalides in good yields.


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