Asymmetric Total Synthesis of (-)-Lundurine B and Determination of Its Absolute Stereochemistry

作者：Nakajima Masaya; Arai Shigeru; Nishida Atsushi^*

来源：Chemistry-An Asian Journal, 2015, 10(4): 1065-1070.

DOI：10.1002/asia.201403407

• alkaloids
• asymmetric synthesis
• lundurine
• natural products
• total synthesis

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.

• 出版日期2015-4