Total Synthesis of (−)-Bucidarasin A Starting from an Original Chiral Building Block
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- Kenji Usui
- Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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- Misaki Kanbe
- Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
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- and Masahisa Nakada
- Department of Chemistry and Biochemistry, Faculty of Science and Engineering, Waseda University 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan
書誌事項
- 公開日
- 2014-09-05
- 資源種別
- journal article
- DOI
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- 10.1021/ol502129u
- 10.1002/chin.201512289
- 公開者
- American Chemical Society (ACS)
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説明
The highly stereoselective total synthesis of (-)-bucidarasin A, which also elucidated the absolute structure of its natural form, is described. The total synthesis features effective use of the original chiral building block prepared by us and a series of highly stereoselective reactions, i.e., hydroxy-directed hydrogenation, [4 + 2] cycloaddition of a sterically hindered dienophile, reduction of ketones, formation of the C9 side-chain diene, and formation of the THF moiety bearing two acetyloxy groups.
収録刊行物
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- Organic Letters
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Organic Letters 16 (18), 4734-4737, 2014-09-05
American Chemical Society (ACS)
