Isolation, Structure Elucidation, and Total Synthesis of Myrtuspirone A from Myrtus communis

作者：Min-Jing Cheng, Xinyi Yang, Jiaqing Cao, Chao Liu, Liping Zhong, Ying Wang, Xuefu You, Chuang‐Chuang Li, Lei Wang, Wen‐Cai Ye · 发表于：Organic Letters · 年份：2019 · DOI：10.1021/acs.orglett.9b00108 · 被引用次数：34 · 研究领域：Axial and Atropisomeric Chirality Synthesis、Chemical synthesis and alkaloids、Phytochemistry and Biological Activities

A pair of enantiomeric triketone-phloroglucinol hybrids, (+)- and (-)-myrtuspirone A (1), featuring an unprecedented 3-isopropyl-3 H-spiro[benzofuran-2,1'-cyclohexane] backbone, were isolated from the leaves of Myrtus communis. The absolute configuration of each enantiomer of 1 was determined by X-ray diffraction and chemical calculations. Furthermore, the gram-scale total syntheses of (±)-1 and (-)-1 were conducted in four steps using a Michael- N-iodosuccinimide (NIS)-mediated (3 + 2)-annulation reaction. Both (+)- and (-)-1 exhibited antibacterial activities against Gram-positive bacteria including multidrug-resistant strains.