The total synthesis of naturally occurring complex polycyclic sesquiterpenes represents a significant challenge in organic chemistry. Stimulated by their interesting and diverse biological properties, the ability to construct such motifs in a concise and economical manner has been the focus of intense research. In this context, the transition metal-catalyzed [m+n+o] carbocyclization reaction represent an important class of reactions, due to their ability to construct polycyclic scaffolds with a high degree of molecular complexity in a single operation. This seminar will focus on recent developments in the rhodium-catalyzed [(3+2)+2] carbocyclization reaction of alkenylidenecyclopropanes with alkynes and its application in the total synthesis of pyrovellerolactone.

Stereoselective synthesis of the polycyclic lactarane skeleton via a rhodium-catalyzed [(3+2)+2] carbocyclization: Total synthesis of pyrovellerolactone

245th National Meeting (2013)

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