Tandem Stereospecific Radical Cation-Mediated Syntheses of Oligostilbenoid Dimers
- Authors: Noel F. Thomas, Kiew C. Lee, Jean Frederic F. Weber, Ibtisam Abdul Wahab, Khalijah Awang, A. Hamid A. Hadi, Pascal Richomme7
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View Affiliations Hide Affiliations7 Department of Chemistry, Faculty of Sciences, Universiti Malaya, 59100 Kuala Lumpur, Malaysia
- Source: Frontiers in Natural Product Chemistry: Volume 1 , pp 19-30
- Publication Date: January 2005
- Language: English
Tandem Stereospecific Radical Cation-Mediated Syntheses of Oligostilbenoid Dimers, Page 1 of 1
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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.
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