Nakajima Masaya, Arai Shigeru, Nishida Atsushi
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuou-ku, Chiba 260-8675 (Japan).
Chem Asian J. 2015 Apr;10(4):1065-70. doi: 10.1002/asia.201403407. Epub 2015 Feb 12.
A total synthesis of the Kopsia tenuis alkaloid (-)-lundurine B has been achieved. A quaternary chiral carbon has been created by an asymmetric deprotonation using a symmetric spiro cyclohexanone intermediate with a chiral lithium amide. The hexacyclic skeleton was sequentially constructed through metal-mediated reactions. The absolute stereochemistry of intermediate 5 has been unambiguously established by X-ray crystallographic analysis. This is the first description of the absolute stereochemistry of Kopsia tenuis alkaloids based on chemical synthesis.
已完成对柯蒲木属生物碱（-）-lundurine B的全合成。使用带有手性锂酰胺的对称螺环己酮中间体，通过不对称去质子化反应生成了一个季碳手性中心。通过金属介导的反应逐步构建了六环骨架。中间体5的绝对立体化学结构已通过X射线晶体学分析明确确定。这是基于化学合成对柯蒲木属生物碱绝对立体化学的首次描述。
