Total synthesis of (S)-(+)-ent-phomapyrones B and surugapyrone B |
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| Authors: | Hiroaki Ohmukai Yasumasa Sugiyama Akira Hirota Mitsunori Kirihata Shinji Tanimori |
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| Institution: | 1. Department of Applied Biological Sciences, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, Osaka, Japan;2. Department of Food and Health Sciences, Jissen Women's University, Hino, Tokyo, Japan;3. School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan |
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| Abstract: | Phomapyrone B ( 1 ), the 2-pyrones isolated from the phytopathogenic fungus Leptosphaeria maculans, has been synthesized as the enantiomeric form starting from (S)-2-methylbutanol ( 4 ). Surugapyrone B ( 3 ) isolated from Streptmyces sp. USF-6280 as an antioxidant has also been synthesized as a natural form. The absolute configuration of phomapyrone B ( 1 ) was estimated to be the (R)-form and that of surugapyrone B ( 3 ) being the (S)-form. A series of 2-pyrone derivatives 17 have been synthesized through the established procedure and their DPPH radical-scavenging activities have also been evaluated. |
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