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Enantioselective Synthesis of 15-Deoxy-Δ12,14-Prostaglandin J2.
Li, Jiaming; Stoltz, Brian M; Grubbs, Robert H.
Afiliação
  • Li J; The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , United States.
  • Stoltz BM; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering , California Institute of Technology , 1200 East California Boulevard, MC 101-20 , Pasadena , California 91125 , United States.
  • Grubbs RH; The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , United States.
Org Lett ; 21(24): 10139-10142, 2019 12 20.
Article em En | MEDLINE | ID: mdl-31808699
ABSTRACT
An enantioselective synthesis of 15-deoxy-Δ12,14-prostaglandin J2 is reported. The synthesis begins with the preparation of enantiopure 3-oxodicyclopentadiene by a lipase-mediated kinetic resolution. A three-component coupling followed by a retro-Diels-Alder reaction provides the C8 stereochemistry of the prostaglandin skeleton with high enantioselectivity. Stereoretentive olefin metathesis followed by a Pinnick oxidation affords 15-deoxy-Δ12,14-prostaglandin J2 in high enantiopurity.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Prostaglandina D2 Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Prostaglandina D2 Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Estados Unidos