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Synthesis of the Carbocyclic Core of Massadine
Chunrui Sun1, Hyunjin Lee1, Daesung Lee1
1Department of Chemistry, University of Illinois at Chicago , 845 West Taylor Street, Chicago, Illinois 60607, United States.
Abstract:
The carbocyclic core of massadine has been synthesized relying on a stereoselective formal [3 + 2] cycloaddition of lithiumtrimethylsilyldiazomethane with α,β-unsaturated esters to form a Δ(2)-pyrazoline moiety followed by facile N-N bond cleavage. A unique feature of the current approach is the direct installation of the tertiary α-amino center and a β-cyano group in a cis arrangement on the resulting cyclopentane framework via a previously developed formal aminocyanation protocol.
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