(+) -アンフィディノリドA.の全合成 構造の解明と合成の完成
Barry M Trost1, Paul E Harrington, John D Chisholm
1Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Journal of the American Chemical Society
|September 30, 2005
まとめ
細胞毒性マクロリド (+) -アンフィディノリドAの全合成は,ルテニウム触媒結合を用いて達成した. この方法は,合成ダイアステロエーマーのNMR分析を通じて,天然製品の正しいステレオ化学を確認しました.
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 自然製品の合成
- 化学生物学 化学生物学とは
背景:
- (+) -アンフィディノリドAは,複雑な20個の環構造を持つ細胞毒性マクロリドです.
- このような天然製品の正確なステレオ化学を明らかにすることは,それらの生物学的活動を理解し,合成の努力をするために不可欠です.
研究 の 目的:
- (+) -アンフィディノリドAの全合成を達成するために.
- 自然製品の提案された構造と相対的なステレオ化学を確認するために.
- 複雑なマクロライドの効率的な合成戦略を開発する.
主な方法:
- ルテニウムで触媒化されたアルケン-アルキン結合はC15-C16結合を形成するために使用され,20個のマクロラクトン環を構成しました.
- 提案された構造から,アンフィディノリドAの様々なダイアステロエーマーを合成する.
- 合成アイソマーと天然製品を比較するための核磁気共鳴 (NMR) 化学シフト分析.
主要な成果:
- (+) -アンフィディノリドAの完全な合成が成功しました.
- NMR化学シフトの偏差を分析することによって,当初報告されたステレオ化学における構造的エラーの特定.
- 合成化合物のスペクトル測定データは,自然素材との優れた一致を示し,修正された構造を確認しました.
結論:
- (+) -アンフィディノリドAの構造と相対的ステレオ化学は,全合成とNMR分析によって決定的に確立されています.
- 合成経路は,アンフィディノリドAおよびその類似品へのアクセスに信頼できる方法を提供します.
- この研究は,複雑な自然産物の構造解明とステレオ化学的割り当てにおけるNMR化学シフト分析の有用性を検証しています.
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