Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India.
Org Biomol Chem. 2019 Aug 28;17(32):7507-7516. doi: 10.1039/c9ob01426h. Epub 2019 Jul 31.
Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N, isolated from the Myrtaceae family, were accomplished in a convergent fashion in 5, 5, 1, 1, and 3 steps, respectively. A highly regio- and diastereoselective oxidative [3 + 2] cycloaddition reaction of acylphloroglucinols with α-phellandrene, diastereoselective modified Friedel-Crafts reaction of acylphloroglucinols with piperetol, and stereoselective epoxidation of extremely hindered β-face were described as key reactions.
受生物启发的对映选择性全合成 (-)-viminalins A、B、H、I 和 N，这些化合物分离自桃金娘科植物，以 5、5、1、1 和 3 步的方式分别实现了收敛式合成。高度区域和立体选择性的酰基间苯三酚与α-松油烯的氧化 [3 + 2] 环加成反应、酰基间苯三酚与胡椒醇的立体选择性改良 Friedel-Crafts 反应，以及极其受阻的β-面的立体选择性环氧化反应被描述为关键反应。
