Asymmetric Total Synthesis of (−)‐Lundurine B and Determination of Its Absolute Stereochemistry. Issue 4 (12th February 2015)

• Record Type: Journal Article
• Authors: Nakajima, Masaya; Arai, Shigeru; Nishida, Atsushi
• Is Part Of: Chemistry, an Asian journal. Volume 10:Issue 4(2015:Apr.)
• Page Start: 1065
• Page End: 1070
• Publication Date: 2015-02-12
• Subjects: alkaloids -- asymmetric synthesis -- lundurine -- natural products -- total synthesis; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201403407
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: 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 intermediate5 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. Abstract : Lord of the rings : The total synthesis of the alkaloid (−)‐Lundurine B has been accomplished in 1.23 % yield through a linear 30 step synthesis including desymmetric deprotonation with a chiral lithium amide, metal‐catalyzed and metal‐mediated formation of the C, D, and F rings.