Au(I)-Catalyzed Cyclization of Epoxyalkynes to Allylic Alcohol Containing Spiroketals and Application to the Total Synthesis of (-)-Alotaketal A.

Lee, Jaeyeon; Kim, Jiheon; Lee, Hee-Yoon

Lee, Jaeyeon; Kim, Jiheon; Lee, Hee-Yoon.

Afiliación

Lee J; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Dajeon 34141, Republic of Korea.
Kim J; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Dajeon 34141, Republic of Korea.
Lee HY; Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Dajeon 34141, Republic of Korea.

Org Lett ; 22(11): 4073-4077, 2020 06 05.

Article en En | MEDLINE | ID: mdl-32391700

RESUMEN

A gold-catalyzed tandem spiroketalization of epoxyalkynes accompanied by epoxide rearrangement into the corresponding allylic alcohol was developed for the construction of functionalized spiroketals. This new synthetic methodology for unsaturated spiroketals warranted a facile total synthesis of alotaketal A from carvone via a corresponding epoxyalkyne precursor.

Asunto(s)

Alquinos/química; Compuestos Epoxi/química; Furanos/química; Oro/química; Propanoles/química; Sesterterpenos/síntesis química; Compuestos de Espiro/química; Catálisis; Ciclización; Estructura Molecular; Sesterterpenos/química; Estereoisomerismo

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Compuestos de Espiro / Propanoles / Alquinos / Compuestos Epoxi / Sesterterpenos / Furanos / Oro Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article

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