Regiodivergent Hydration–Cyclization of Diynones under Gold Catalysis

Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration− oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting...

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Bibliographic Details
Authors: Solas Luera, Marta, Muñoz Torres, Miguel Ángel, Suarez Pantiga, Samuel, Sanz Díez, Roberto
Format: article
Status:Versión aceptada para publicación
Publication Date:2020
Country:España
Institution:Universidad de Burgos (UBU)
Repository:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/5533
Online Access:http://hdl.handle.net/10259/5533
Access Level:Open access
Keyword:Hydrocarbons
Cyclization
Mixtures
Catalysts
Selectivity
Química orgánica
Chemistry, Organic
Description
Summary:Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration− oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated.