Michaei acceptor

Copper-mediated Addition Reactions to Extended Michaei Acceptors I 1 3... 

The synthesis of both enantiomers of the antitumor-antibiotic fredericamycin A was achieved in the laboratory of D.L. Boger. The DE ring system of the natural product was assembled via a tandem Michael addition-Dieckmann condensation. The highly substituted 4-methylpyridine precursor was treated with excess LDA followed by the addition of the Michaei acceptor cyciopentenone. The Michael adduct underwent an intramolecular acylation with the ester functionaiity in situ to afford the desired DEF tricycie. 

Bind to Michaei acceptor via H-bonding) Stabiiize deveioping negative charge during the Michaei addition... 

Summary This is an exampie of enoiate addition using a Michaei acceptor as eiectrophiie ... 

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