A wide range of transformations that involve alkynes are initiated by either an electrophilic or a transition-metal-catalyzed activation step. This is especially prevalent in domino reactions where alkyne activation is directly followed by an internal nucleophilic attack to construct carbocyclic and heterocyclic molecules of enhanced complexity.This contribution will describe our work on the reactivity of 1,5-enynes in electrophilic cyclizations that proceed through iodonium-activation. In this context, the formation of several carbocyclic compounds including aryls is discussed, as well as the total synthesis of cybrodol. Additionally, novel findings regarding the noble-metal-catalyzed reactivity of 1,5-enynes and their heteroatom analogues, as well as an application to the total synthesis of cyperolone, will be presented. In these cases, a domino reaction consisting of cyclization and subsequent pinacol-type rearrangement takes place.

Alkyne activation as key strategy for the synthesis of cyclic molecules: Methods and total synthesis

241st National Meeting (2011)

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