Total synthesis of cucurbitoside-like phenolic glycosides by double fluorous and acyl mixture synthesis |
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Authors: | Masaru Kojima Yutaka NakamuraKazuki Komori Shoji AkaiKen-ichi Sato Seiji Takeuchi |
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Institution: | a Niigata University of Pharmacy and Applied Life Sciences, 265-1 Higashijima, Akiha-ku, Niigata 956-8603, Japan b Material and Life Chemistry, Faculty of Engineering, Kanagawa University, 3-27-1 Rokkakubashi, Kanagawa-ku, Yokohama 221-8686, Japan |
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Abstract: | The first and simultaneous total syntheses of cucurbitosides A, B, G, and I, seguinosides C and D, and two unnatural analogs were achieved using the technique of fluorous mixture synthesis. The eight precursors of cucurbitoside-like phenolic glycosides were prepared by glycosylation of a mixture of two glucopyranosyl acceptors bearing different fluorous benzyl groups with a mixture of four apiofuranosyl donors bearing benzoyl, 3-methylbutyryl, 4-benzyloxybenzoyl, and 4-nitrobenzoyl groups, followed by a single run of HPLC with serially connected Fluophase® RP and Inertsil® ODS-3 columns. Finally, the individual pure disaccharide precursors were detagged to yield the eight cucurbitoside-like phenolic glycosides. |
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Keywords: | Total synthesis Acylated phenolic glycosides Fluorous Mixture synthesis |
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