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ハリコンドリンBの全合成に対する逆アプローチ

K C Nicolaou¹, Saiyong Pan¹, Yogesh Shelke¹

¹Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, Texas 77005, United States.

Journal of the American Chemical Society

|June 9, 2021

まとめ

研究者はC−C結合の前にC−O結合を形成することで,ハリコンドリンBを合成する新しい戦略を開発した. ニコラス反応を利用したこの新しいアプローチは,複雑なハリコンドリンとエリブリンファミリー化合物を生成するための改良された方法を提供します.

科学分野:

有機化学
合成化学
薬剤化学

背景:

ハリコンドリンBは重要な治療力を持つ複雑な天然製品です.
ハリコンドリンBの伝統的な合成戦略は,連続したC−C結合形成とC−O結合形成を伴う.
効率的でコンバージェントな合成経路の開発は依然として重要な課題です.

研究の目的:

ハリコンドリンBの新合成戦略を導入する
合成におけるC−OとC−C結合の形成の古典的な順序を逆転させる.
ハリコンドリンとエリブリン系の化合物を合成する新たな機会を探求する.

主な方法:

ニコラス反応を利用して線形エーテルを生成した
主要な断片 (I,MN,EFG,A) の結合を伴うコンバージェント・シンセシス・アプローチを使用した.
重要なステップは,C-C結合形成の前にC-O結合形成であり,その後にマクロラクトニゼーションが続きます.

主要な成果:

定義された断片 I,MN,EFG,Aを合成した.
これらの断片をIJKLMNとEFGHIJKLMNに組み立てました
ハリコンドリンBの全合成を短く収束した経路で完了した.

結論:

C-C結合形成前にC-O結合形成の逆戦略は,ハリコンドリンB合成に有効である.
この新しいアプローチは,ハリコンドリンとエリブリン類により効率的で柔軟な経路を提供します.
開発された方法論は,複雑な多環化合物へのアクセスのための新しい道を開きます.

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