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(+) リアノドルの15段階の合成

Kangway V Chuang¹, Chen Xu¹, Sarah E Reisman²

¹Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, CA 91125, USA.

Science (New York, N.Y.)

|August 27, 2016

まとめ

複合的なディターペノイドである (+) - ライオノドルは15段階で合成された. ライオジン受容体調節器を合成するためのこの効率的な方法は,迅速な炭素フレームワークの構築と酸素の設置のための重要な反応を使用します.

科学分野:

有機化学
分子生物学
バイオ物理学

背景:

(+) -ライオノジンと (+) -ライオノドルは,ライオノジン受容体を通して細胞内カルシウムイオン放出を調節する複合的ディテルペノイドである.
リアノジン受容体は,筋肉の刺激と収縮の結合とシナプス伝達に不可欠です.
これらのディターペノイドの構造的変異は,ライアノジン受容体イソフォームに対する結合親和性と選択性に影響を与える可能性があります.

研究の目的:

(+) リアノドルの簡潔で効率的な化学合成を開発する.
ポリヒドロキシル化テルペンの合成を効率化するための戦略的C-O結合構造を探求する.

主な方法:

(S) -プレゴンから (+) -ライアノドルを15ステップで合成する.
パウソン・カンド反応を用いて素早く炭素フレームを組み立てました
3つの酸素原子を同時に設置するために,SeO2媒介による酸化を使用しています.

主要な成果:

(+) リアノドルを合成し,ステップの数を大幅に減らした.
この合成におけるパウソン・カンド反応とSeO2媒介による酸化の効率を証明した.
戦略的C-Oボンドの重要性を強調した.

結論:

(+) リアノドルの短時間かつ効率的な合成が達成された.
この合成経路は,保護グループと酸化還元調整の必要性を最小限にします.
この戦略は,他のポリヒドロキシル化テルペンの合成に適用できます.

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