Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5215144 | Tetrahedron | 2015 | 10 Pages |
Abstract
The ABC-ring system of calyciphylline A-type alkaloids has been synthesized. The key steps of the synthetic approach are an atom transfer radical cyclization of a trichloroacetamide upon an enol acetate to generate the B ring, and a sulfone-based conjugated addition upon a β-methyl-α,β-unsaturated ketone to give the target azatricyclic ketone. Selecting the cation (K+ or Cs+) of the carbonate in the C ring-forming intramolecular Michael addition gives stereodivergent access to both epimers of the cyclized product.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Faïza Diaba, AgustÃn MartÃnez-Laporta, Guilhem Coussanes, Israel Fernández, Josep Bonjoch,