Frontiers in Natural Product Chemistry

Volume: 1

Tandem Stereospecific Radical Cation-Mediated Syntheses of Oligostilbenoid Dimers

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

Pp: 19-30 (12)

DOI: 10.2174/978160805212710501010019


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

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