Department of Chemistry and Biochemistry, Baylor University, One Bear Place 97348, Waco, TX, 76798, USA.
Angew Chem Int Ed Engl. 2018 Feb 12;57(7):1991-1994. doi: 10.1002/anie.201712369. Epub 2018 Jan 17.
Described herein is a synthetic strategy for the total synthesis of (±)-phomoidride D. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels-Alder cycloaddition. A subsequent SmI -mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.
本文描述了(±)-phomoidride D 的全合成的一种综合策略。这种高效和立体选择性的方法通过串联酚氧化/分子内 Diels-Alder 环加成,快速组装碳环核心。随后 SmI -介导的环化级联反应提供了一个 isotwistane 中间体,有利于 Wharton 断裂,揭示了所需的双环[4.3.1]癸烯骨架,并为合成完成奠定了基础。