Jung Youngeun, Kim Ikyon
College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University, 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea.
Org Biomol Chem. 2015 Apr 14;13(14):4331-5. doi: 10.1039/c5ob00216h. Epub 2015 Mar 13.
A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling of allylic acetate with arylboronic acid provided direct access to 3-benzylchromene which was converted to the target molecule upon ensuing dihydroxylation and acid-catalyzed cyclization in a highly concise manner.
从7-甲氧基色烯出发，开发了一条6步合成巴西灵三甲醚的短路线，总收率为78%。在7-甲氧基色烯上区域选择性地引入甲酰基，然后进行还原和乙酰化，得到烯丙基乙酸酯。烯丙基乙酸酯与芳基硼酸的钯催化烯丙基偶联反应直接得到3-苄基色烯，随后通过双羟基化和酸催化环化以高度简洁的方式将其转化为目标分子。
