Frontiers in Natural Product Chemistry

Volume: 1

Indexed in: EBSCO.

“Frontiers in Natural Product Chemistry” is an Ebook series devoted to publishing the latest and most important advances in natural product chemistry. The Ebook series covers all aspects of ...
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Tandem Stereospecific Radical Cation-Mediated Syntheses of Oligostilbenoid Dimers

Pp. 19-30 (12)

Noel F. Thomas, Kiew C. Lee, Jean-Frederic F. Weber, Ibtisam Abdul Wahab, Khalijah Awang, A. Hamid A. Hadi and Pascal Richomme

Abstract

Protected trihydroxystilbenes have been synthesized by Heck coupling methodology in three steps. Treatment of 3,4-dimethoxy-12-benzyloxymethyl stilbene with ferric chloride in dichloromethane (room temperature), gave catechol analogues of ampelopsin F and of restrytisol C, while 3,4-dimethoxy-12- acetoxymethyl stilbene treated in the same conditions yielded two other analogues of restrytisol C (but no trace of ampelopsin F analogues). All the structures were unambiguously confirmed by 1D- and 2D- homo- and heteronuclear nmr experiments. All transformations were stereospecific. The ampelopsin F-type compounds are the result of radical cation pathways. By contrast, the restrytisol Ctype compounds are the products of pericyclic pathways.

Keywords:

oligostilbenoids, protein kinase c inhibitor, stilbene, phenanthrene ring, lactonization, synthesis

Affiliation:

Department of Chemistry, Faculty of Sciences, Universiti Malaya, 59100 Kuala Lumpur, Malaysia.