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全体の合成,構造の改定,および (-) - ブレベナルの絶対的構成
Haruhiko Fuwa1, Makoto Ebine, Andrea J Bourdelais
1Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, Aoba-ku, Sendai 981-8555, Japan.
Journal of the American Chemical Society
|December 21, 2006
まとめ
研究者らは,海洋ポリエーテル天然産物であるブレヴェナル (brevenal) の全合成を達成した. 構造分析により,自然産物は当初提案された構造のエピマーである可能性が明らかになり,現在合成によって確認されています.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 自然製品合成 自然製品合成
- 海洋自然産物 海洋自然産物
背景:
- ブレヴェナル (Brevenal) は,Karenia brevis.から分離された無毒のポリサイクルエーテル天然製品です.
- ブレヴェナルの当初提案された構造には,決定的な立体化学的割り当てが欠けていた.
研究 の 目的:
- 提案されたブレヴェナル構造の全合成を達成するために.
- 顕微鏡データと合成に基づいたブレヴェナルの構造を修正し,確認する.
- 自然製品の絶対的な構成を確立するために.
主な方法:
- Suzuki-Miyaura カップリングを使用して,ペンタサイクリックポリエーテル骨格の収束組み立て.
- 銅 (((I) チオフェン-2-カルボキシラート (CuTC) 促進された改変されたスティルカップリングによるダイナルサイドチェーンのステレオ選択的構築.
- 合成化合物と天然製品間の詳細なNMRスペクトロスコピーの比較.
主要な成果:
- 当初提案された構造 (1) の総合合成が完了しました.
- NMRスペクトルの不一致は,構造的修正が必要であることを示した.
- 自然産物は,提案された構造のC26エピマー (2) として特定されました.
- 改訂された構造 (2) は,完全な合成によって検証され,絶対的構成が確認されました.
結論:
- ブレヴェナルとそのエピマーの全合成は,構造的およびステレオ化学的割り当てを決定的に提供します.
- この研究は,重要な海洋ポリエーテルであるブレヴェナル (brevenal) の既知の構造を修正しています.
- 開発された合成戦略は,他の複雑なポリサイクルエーテル天然製品にも適用できます.
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