Hyunjin Lee
UIC
The carbocyclic core of massadine has been synthesized relying on a stereoselective formal [3+2]–cycloaddition of lithiumtrimethylsilyldiazomethane with, alpha beta-unsaturated esters to form a pyrazoline moiety followed by facile N–N bond cleavage. A unique feature of the current approach is the direct installation of the tertiary alpha-amino center and a beta-cyano group in cis arrangement on the resulting cyclopentane framework via a previously developed formal aminocyanation protocol.