Total Synthesis of Terpioside B |
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| Authors: | Kazuki Inaba Masato Endo Naoto Iibuchi Prof?Dr Daisuke Takahashi Prof?Dr Kazunobu Toshima |
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| Institution: | Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522 Japan |
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| Abstract: | The first total synthesis of terpioside B ( 1 ) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2-cis-glycosidic linkages. Thus, α(1,4)-linked d -galactoside was effectively constructed from a 1,2-anhydrogalactose donor and an unprotected 1,6-anhydrogalactose acceptor by using a boron-mediated aglycon delivery (BMAD) method. In addition, α-l -fucofuranosides were stereoselectively and simultaneously constructed by remote group-assisted 1,2-cis-α-stereoselective glycosylations. |
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| Keywords: | boron-mediated aglycon delivery glycosphingolipids glycosylation terpioside B total synthesis |
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