書誌事項
- タイトル別名
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- Total Synthesis of Otteliones Possessing Powerful Tubulin Polymerization Inhibitory Activity
- キョウリョク ナ チューブリン ジュウゴウ ソガイ カッセイ オ ユウスル オッテリオンルイ ノ ゼンゴウセイ
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Otteliones A and B, isolated from the fleshwater plant Ottelia alismoides, were found to exhibit extremely potent growth-inhibitory activity against human cancer cell lines. Structurally, these small-molecule natural products possess a novel bicyclic hydrindane skeleton with four contiguous asymmetric carbon centers, in which the rare and sensitive 4-methylene-2-cyclohexenone substructure is a special characteristic feature. When these natural products were isolated, the relative configuration of ottelione B was determined; however, ottelione A could not been assigned unambiguously. In this article, we describe the first enantioselective total synthesis of (+)-ottelione A, (-)-ottelione B, and (+)-3-epi-ottelione A (the earlier proposed stereostructure of ottelione A) using a flexible synthetic scheme that allows an access to all possible stereostructures of ottelione A. The present total synthesis has fully established the absolute configuration of these natural products. In addition, the cell growth inhibition analysis and tubulin polymerization assay of the synthesized otteliones are also described.
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 67 (9), 909-920, 2009
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
- 1390282680288800000
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- NII論文ID
- 10025400251
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BD1MXht1WgtLbI
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 10384818
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- NDL
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- 抄録ライセンスフラグ
- 使用不可