化学
对映选择合成
全合成
分子内力
立体选择性
紫罗兰酮
呼吸
刺激
立体化学
有机化学
催化作用
植物
生物
神经科学
作者
Hendrik Helmut Bulthaupt,Fabian Glatz,Sven Michael Papidocha,Chen Wu,SS Teh,Susanne Wolfrum,Lucia Balážová,Christian Wolfrum,Erick M. Carreira
摘要
We report the first and enantioselective total syntheses of (+)-1-deacetylcaesalmin C, (+)-δ-caesalpin, (+)-norcaesalpinin MC, and (+)-norcaesalpinin P. Salient features of the synthetic strategy are an exo-selective intramolecular Diels-Alder reaction of a furanoquinone monoketal and subsequent chemoselective reduction of the resulting pentacyclic furfuryl ketal, furnishing a keystone intermediate. The latter enables access to the collection of natural products through implementation of stereoselective oxidations. Having accessed the cassane furanoditerpenoids, we unveil previously unknown bioactivity: (+)-1-deacetylcaesalmin C stimulates respiration in brown adipocytes, which has been suggested to play a central role in treatment of obesity.
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