First Total Synthesis of Inaoside A
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Front Cover: First Total Synthesis of Inaoside A (Asian J. Org. Chem. 12/2024)
- Volume 13Issue 12Asian Journal of Organic Chemistry
- First Published online: December 13, 2024
Tomoya Takao
Department of Agriculture Graduate, School of Science and Technology, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
These two authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Atsushi Kawamura
Department of Biomolecular Innovation, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
These two authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Hidefumi Makabe
Department of Biomolecular Innovation, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
Department of Agriculture Graduate, School of Science and Technology, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
Search for more papers by this authorTomoya Takao
Department of Agriculture Graduate, School of Science and Technology, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
These two authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Atsushi Kawamura
Department of Biomolecular Innovation, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
These two authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Hidefumi Makabe
Department of Biomolecular Innovation, Institute for Biomedical Sciences, Interdisciplinary Cluster for Cutting Edge Research, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
Department of Agriculture Graduate, School of Science and Technology, Shinshu University, Kami-ina, Nagano, 399-4598 Japan
Search for more papers by this authorAbstract
The first total synthesis of inaoside A, an α-d-ribofuranoside isolated by our group from the edible mushroom Laetiporus cremeiporus, is described. The key reaction was an α-selective Schmidt glycosylation. Most reported syntheses of ribofuranosides following the general Schmidt glycosylation procedure preferentially give β-ribofuranosides. In contrast, using a 2,3,5-tri-O-(tert-butyldimethylsilyl)-protected ribofuranoside substrate, which is easy to prepare and can be deprotected after glycosylation, revealed that the α-ribofuranoside was preferentially obtained.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.
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