Stereoselective Total Synthesis of Aspergillide A: A Visible Light-Mediated Photoredox Access to the Trisubstituted Tetrahydropyran Core.

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ID: 26451
2019
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Abstract
A stereoselective total synthesis of natural product aspergillide A is reported. The adopted strategy relies on the direct access to the key tetrahydropyran core through a visible light-mediated photoredox reaction from an allylic alcohol and iodoacetic acid. In a single manipulation, a γ-iodo-δ-valerolactone is obtained through an atom transfer radical addition followed by in situ acid-catalyzed lactonization. The obtained lactone possesses three functionalized sites, which were seized to link the required substituents in the final product and thus completing the total synthesis of aspergillide A.
Reference Key
mateusruiz2019stereoselectivethe Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Mateus-Ruiz, Jeferson B;Cordero-Vargas, Alejandro;
Journal The Journal of organic chemistry
Year 2019
DOI
10.1021/acs.joc.9b01705
URL
Keywords Keywords not found

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