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Total Synthesis of (±)‐Phomoidride D
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-01-17 , DOI: 10.1002/anie.201712369
Joyce C. Leung 1 , Aaron A. Bedermann 1 , Jón T. Njardarson 1 , David A. Spiegel 1 , Graham K. Murphy 1 , Naoto Hama 1 , Barry M. Twenter 1 , Ping Dong 1 , Tatsuya Shirahata 1 , Ivar M. McDonald 1 , Munenori Inoue 1 , Nobuaki Taniguchi 1 , Travis C. McMahon 1 , Christopher M. Schneider 1 , Nancy Tao 1 , Brian M. Stoltz 1 , John L. Wood 1
Affiliation  

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 SmI2‐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.

中文翻译:

(±)-拟苯甲醛D的全合成

本文描述了一种全合成(±)-磷脂酰D的合成策略。这种高效且立体选择性的方法通过串联酚醛氧化/分子内Diels-Alder环加成法提供了碳环核的快速组装。随后的SmI 2介导的环化级联反应提供了异沃顿中间体,可用于沃顿断裂,从而揭示必需的双环[4.3.1]癸烯骨架,并为合成完成奠定了基础。
更新日期:2018-01-17
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