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Synthesis of 3-epi-Hypatulin B Featuring a Late-Stage Photo-Oxidation in Flow.
Leisering, Stefan; Ponath, Sebastian; Shakeri, Kamar; Mavroskoufis, Alexandros; Kleoff, Merlin; Voßnacker, Patrick; Steinhauer, Simon; Weber, Manuela; Christmann, Mathias.
Afiliación
  • Leisering S; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Ponath S; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Shakeri K; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Mavroskoufis A; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Kleoff M; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Voßnacker P; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Steinhauer S; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Weber M; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
  • Christmann M; Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195 Berlin, Germany.
Org Lett ; 24(24): 4305-4309, 2022 06 24.
Article en En | MEDLINE | ID: mdl-35536108
A synthesis of 3-epi-hypatulin B, a highly oxygenated and densely functionalized bicyclic scaffold, is reported. The carbon skeleton was prepared by functionalization of a cyclopentanone and an intramolecular Mukaiyama aldol reaction. Highlights include a late-stage photo-oxidation of a methoxyallene to provide an ester group. The problems encountered in the batch process were solved by translation into a flow protocol. Our synthesis highlights the value of flow chemistry to enable challenging late-stage transformations in natural product synthesis.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Productos Biológicos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Productos Biológicos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Alemania Pais de publicación: Estados Unidos