Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis.

Hutchings-Goetz, Luke S; Yang, Chao; Fyfe, James W B; Snaddon, Thomas N

Hutchings-Goetz, Luke S; Yang, Chao; Fyfe, James W B; Snaddon, Thomas N.

Afiliación

Hutchings-Goetz LS; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN, 47405, USA.
Yang C; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN, 47405, USA.
Fyfe JWB; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN, 47405, USA.
Snaddon TN; Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN, 47405, USA.

Angew Chem Int Ed Engl ; 59(40): 17556-17564, 2020 09 28.

Article en En | MEDLINE | ID: mdl-32476195

RESUMEN

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (-)-akuammicine and (-)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Asunto(s)

Alcaloides/química; Chelidonium/química; Strychnos/química; Alcaloides/síntesis química; Alquilación; Benzofenantridinas/síntesis química; Benzofenantridinas/química; Alcaloides de Berberina/síntesis química; Alcaloides de Berberina/química; Catálisis; Chelidonium/metabolismo; Humanos; Indoles/síntesis química; Indoles/química; Iridio/química; Paladio/química; Sirtuina 1/antagonistas & inhibidores; Sirtuina 1/metabolismo; Estereoisomerismo; Estricnina/síntesis química; Estricnina/química; Strychnos/metabolismo; Tiourea/química

Palabras clave

alkaloids; alkylation; cooperative catalysis; iridium; palladium

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Chelidonium / Strychnos / Alcaloides Límite: Humans Idioma: En Revista: Angew Chem Int Ed Engl Año: 2020 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Alemania

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