Synthetic model of a new deoxybenzoin derivative from Deguelia hatschbachii A.M.G. Azevedo
In this paper we describe the synthesis of 2´,4´-dimethoxy-8-(propyl-2-one)-deoxybenzoin, a new compound employed as a model for the comparison with the respective spectral data for 6',4-dihydroxy-3'-(3,3- dimethylallyl)-2",2"-dimethylchromene(5",6":5',4')-2'-methoxy-8-(propyl-2-one) deoxybenzoin, recently isolated from Deguelia hatschbachii A.M.G. Azevedo. Both compounds have a "propyl-2-one" group attached to C-8 of the deoxybenzoin skeleton, for which there is no precedent in the literature. The Friedel-Crafts reaction of 1,3-dimethoxybenzene with phenylacetyl chloride furnished 2´,4´-dimethoxydeoxybenzoin, that after reaction with allyl bromide gave 2´,4´-dimethoxy-8-(allyl)-deoxybenzoin . Wacker oxidation gave the desired model compound in 15% overall yield. The corresponding spectral data reinforced the structure previously determined for the natural product.
| Main Authors: | , , , |
|---|---|
| Format: | Digital revista |
| Language: | English |
| Published: |
Fundação Editora da Universidade Estadual Paulista Júlio de Mesquita Filho - UNESP
2005
|
| Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-46702005000100006 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|