An acid-catalyzed ring-switch reaction of lactams to lactones: concise synthesis of 2,4-dialkyl-3-hydroxybutanolides |
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| Authors: | Chiaki Yamauchi Rumiko Shimazawa Kiyomi Kakiuchi |
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| Affiliation: | a Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), Takayama, Ikoma, Nara 630-0192, Japan
b Faculty of Pharmaceutical Science, Doshisha Women's College of Liberal Arts, Kodo, Kyotanabe, Kyoto 610-0395, Japan |
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| Abstract: | A novel approach for the synthesis of 2,4-dialkyl-3-hydroxybutanolides, having three successive stereogenic centers, by an acid-catalyzed ring-switch reaction of 2-(2-hydroxyalkyl)lactams is described. This transformation was applied to the synthesis of the key intermediates of teromerase inhibitor UCS1025A. |
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