Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 44, Pages 16720-16735Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja409013m
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Funding
- NSF
- NIH [GM 033049]
- W.S. Johnson Graduate Fellowship
- Feodor-Lynen fellowship of the Alexander von Humboldt Foundation
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1145236] Funding Source: National Science Foundation
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The marcfortines are complex secondary metabolites that show potent anthelmintic activity and are characterized by the presence of a bicyclo[2.2.2]diazaoctane fused to a spirooxindole. Herein, we report the synthesis of two members of this family. The synthesis of marcfortine B utilizes a carboxylative TMM cycloaddition to establish the spirocyclic core, followed by an intramolecular Michael addition and oxidative radical cyclization to access the strained bicyclic ring system. In addition, the first asymmetric synthesis of (-)-marcfortine C is described. The key step involves a cyano-substituted TMM cycloaddition, which proceeds in nearly quantitative yield with high diastereo- and enantioselectivity. The resulting chiral center was used to establish all remaining stereocenters in the natural product.
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