Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C
•Key intermediate 9 was prepared from d-(−)-isoascorbic acid as well as d-ribose.•Bio-active compounds 1, 4, and 5 were obtained from a common intermediate 18.•Grubbs RCM, Morita–Baylis–Hillman (MBH), and Luche reductions are key steps. Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B,...
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Veröffentlicht in: | Carbohydrate research 2014-03, Vol.388, p.130-137 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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Zusammenfassung: | •Key intermediate 9 was prepared from d-(−)-isoascorbic acid as well as d-ribose.•Bio-active compounds 1, 4, and 5 were obtained from a common intermediate 18.•Grubbs RCM, Morita–Baylis–Hillman (MBH), and Luche reductions are key steps.
Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(−)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita–Baylis–Hillman (MBH) reaction, and Luche reduction. |
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ISSN: | 0008-6215 1873-426X |
DOI: | 10.1016/j.carres.2013.08.008 |