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Pot-Economical Total Synthesis of Clinprost.
Umekubo, Nariyoshi; Hayashi, Yujiro.
Afiliación
  • Umekubo N; Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
  • Hayashi Y; Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8578, Japan.
Org Lett ; 22(23): 9365-9370, 2020 12 04.
Article en En | MEDLINE | ID: mdl-33231082
ABSTRACT
The pot-economical synthesis of clinprost is reported, in which the core bicyclo[3.3.0]octenone structure was synthesized by two key

steps:

an asymmetric domino Michael/Michael reaction catalyzed by diphenylprolinol silyl ether and an intramolecular Horner-Wadsworth-Emmons reaction. The trisubstituted endocyclic alkene was selectively introduced by 1,4-reduction followed by trapping of the generated enolate with Tf2NPh and subsequent utilization of the Suzuki-Miyaura coupling reaction. Chiral, nonracemic clinprost was synthesized in seven pots with a 17% total yield and excellent enantioselectivity.

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Health_economic_evaluation Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Japón

Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Tipo de estudio: Health_economic_evaluation Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Japón