書誌事項
- タイトル別名
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- Formal Total Synthesis of (−)-Taxol
- 公開日
- 2017
- 資源種別
- journal article
- DOI
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- 10.5059/yukigoseikyokaishi.75.1102
- 公開者
- 公益社団法人 有機合成化学協会
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説明
<p>Formal total synthesis of (−)-taxol is described herein. This convergent synthesis was accomplished by utilizing two chiral fragments, both of which were prepared via asymmetric catalysis. A palladium-catalyzed reaction was found to afford the eight-membered ring effectively, i.e., a B-alkyl Suzuki-Miyaura coupling reaction and an intramolecular alkenylation of a methyl ketone successfully constructed the B-ring of taxol in excellent yield. During the preparation of a substrate for the palladium-catalyzed reaction, a unique rearrangement of the epoxy benzyl ether, via a 1,5-hydride shift that generates the C3 stereogenic center and subsequently forms the C1-C2 benzylidene moiety, was observed. Strenuous efforts were required for transformations after the construction of the taxane scaffold to achieve the formal total synthesis of taxol because very few approaches are available for the synthesis of the target compound.</p>
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 75 (11), 1102-1114, 2017
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390001205339659136
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- NII論文ID
- 130006196258
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 028690029
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- 本文言語コード
- en
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- 資料種別
- journal article
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- データソース種別
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- JaLC
- NDLサーチ
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- 抄録ライセンスフラグ
- 使用不可
