Cross‐Coupling Reaction of Saccharide‐Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin |
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Authors: | Dr Kamil Parkan Dr Radek Pohl Prof?Dr Martin Kotora |
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Institution: | 1. Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technická 5, 166 28 Praha 6 (Czech Republic), Fax: (+420)?220444422;2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.?v.?i. Flemingovo 2, 166 10 Prague 6 (Czech Republic);3. Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2 (Czech Republic), Fax: (+420)211‐951‐326 |
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Abstract: | A convenient synthetic pathway enabling D ‐glucal and D ‐galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross‐coupling reactions under Suzuki–Miyaura cross‐coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. |
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Keywords: | C C coupling glycosides natural products protecting groups synthetic methods |
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