First Asymmetric Total Synthesis of Synerazol, an Antifungal Antibiotic, and Determination of Its Absolute Stereochemistry
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- Yujiro Hayashi
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Mitsuru Shoji
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Takasuke Mukaiyama
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Hiroaki Gotoh
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Shinpei Yamaguchi
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Munetaka Nakata
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Hideaki Kakeya
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
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- Hiroyuki Osada
- Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Graduate School of BASE (Bio-Applications and Systems Engineering), Tokyo University of Agriculture and Technology, Naka-cho, Koganei, Tokyo 184-8588, and Antibiotics Laboratory, Discovery Research Institute, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan
書誌事項
- 公開日
- 2005-06-08
- DOI
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- 10.1021/jo050664x
- 10.1002/chin.200549187
- 公開者
- American Chemical Society (ACS)
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説明
[reaction: see text] By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also established. The key steps are racemization-free deprotection of a TIPS group and introduction of a methyl ether by DMD oxidation of the benzylidene moiety in a substrate having a small protecting group.
収録刊行物
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- The Journal of Organic Chemistry
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The Journal of Organic Chemistry 70 (14), 5643-5654, 2005-06-08
American Chemical Society (ACS)
