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
Hauptverfasser: Babu, D. Chanti, Rao, Ch. Bhujanga, Venkatesham, K., Selvam, J. Jon Paul, Venkateswarlu, Y.
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Sprache:eng
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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.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2013.08.008