Total Synthesis of Diocollettines A via an Acid-Promoted Oxa-Michael-Aldol-Acetalization Cascade.

Kawamoto, Misaki; Sato, Shuntaro; Enomoto, Masaru; Ogura, Yusuke; Kuwahara, Shigefumi

Kawamoto, Misaki; Sato, Shuntaro; Enomoto, Masaru; Ogura, Yusuke; Kuwahara, Shigefumi.

Afiliación

Kawamoto M; Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.
Sato S; Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.
Enomoto M; Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.
Ogura Y; Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.
Kuwahara S; Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki-Aza-Aoba , Aoba-ku , Sendai 980-0845 , Japan.

Org Lett ; 21(24): 10099-10101, 2019 12 20.

Article en En | MEDLINE | ID: mdl-31794233

RESUMEN

A diastereo- and enantioselective total synthesis of diocollettines A with an unusual oxygen-containing tricyclic ring system has been achieved in 63% overall yield from commercially available 3-phenylpropanal via four steps. The key feature of the present synthesis is an exclusively diastereoselective cascade sequence composed of a trans-selective oxa-Michael addition of 1,3-dihydroxyacetone to a 2,3-dihydropyrylium ion intermediate, intramolecular aldol-type reaction, and intramolecular acetalization.

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2019 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos

Texto completo

Añadir a Mi BVS

Imprimir

XML

PubMed Links

Buscar en Google