Progresses for accessing alpha’-methoxy-y-pyrone heterocycle: Applications to the synthesis of verticipyrone and aureothin

Michaël de Paolis (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

Focusing on the synthesis and reactivity of alpha’-methoxy-y-pyrone scaffold, a heterocycle found in several natural products, this account presents the state of the art and the progresses made to access it. A recently developed abiotic strategy relied on the desymmetrization of alpha,alpha’-dimethoxy--pyrone, a readily available building block, by conjugate addition with a nucleophile facilitating the construction of the side chain of the target. This transformation was studied with various nucleophiles and the strategy was successfully employed with tributylallylstannane/n-BuLi and 2-lithio-1,3-dithiane to concisely fashion verticipyrone and aureothin, two natural products with interesting biological activities.

Domaines: Chimie

Michaël de Paolis. Progresses for accessing alpha’-methoxy-y-pyrone heterocycle: Applications to the synthesis of verticipyrone and aureothin. Targets in Heterocyclic Systems, 2016, 20, pp.63-84. ⟨10.17374/targets.2017.20.63⟩. ⟨hal-02046200⟩