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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046200
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:36:29 PM
Last modification on : Thursday, July 2, 2020 - 3:30:13 AM

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

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