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- Title
Asymmetric Total Synthesis of (−)-Lundurine B and Determination of Its Absolute Stereochemistry.
- Authors
Nakajima, Masaya; Arai, Shigeru; Nishida, Atsushi
- 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 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.
- Subjects
STEREOCHEMISTRY; CYCLOHEXANONES; PROTON transfer reaction kinetics; X-ray crystallography technique; CHEMICAL synthesis; ENANTIOSELECTIVE catalysis
- Publication
Chemistry - An Asian Journal, 2015, Vol 10, Issue 4, p1065
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201403407