Total syntheses of (+)- and (−)-1,3,4,5-tetragalloylapiitol and revision of absolute configuration of naturally occurring (−)-1,3,4,5-tetragalloylapiitol |
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| Authors: | Masaru Kojima Yutaka NakamuraShoji Akai Ken-ichi SatoSeiji 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 total syntheses of (+)- and (−)-1,3,4,5-tetragalloylapiitol were achieved in seven steps from d- and l-ribose, respectively. By comparing the optical rotations of both enantiomers with those of the natural product, the absolute configuration at C-3 in the naturally occurring 1,3,4,5-tetragalloylapiitol has been revised to R. The absolute configurations at C-3 in the synthetic (+)- and (−)-1,3,4,5-tetragalloylapiitol were further confirmed by the circular dichroism exciton chirality method. |
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| Keywords: | Total synthesis Absolute configuration 2 d-apiitol" target="_blank">3-O-Benzylidene-d-apiitol 1 3 4 5-Tetragalloylapiitol Circular dichroism exciton chirality method |
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