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Total Synthesis and Stereochemical Reassignment of Citrafungin A.
Chen, Zongjia; Robertson, Angus; White, Jonathan M; Rizzacasa, Mark A.
Afiliação
  • Chen Z; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute , The University of Melbourne , 30 Flemington Road , Parkville , Victoria 3010 , Australia.
  • Robertson A; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute , The University of Melbourne , 30 Flemington Road , Parkville , Victoria 3010 , Australia.
  • White JM; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute , The University of Melbourne , 30 Flemington Road , Parkville , Victoria 3010 , Australia.
  • Rizzacasa MA; School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute , The University of Melbourne , 30 Flemington Road , Parkville , Victoria 3010 , Australia.
Org Lett ; 21(23): 9663-9666, 2019 12 06.
Article em En | MEDLINE | ID: mdl-31724869
ABSTRACT
The stereoselective 12-step total synthesis of the reassigned structure for citrafungin A (1a) via cyclobutene diester 10 is described. Key steps involved a formal [2 + 2]-cycloaddition, oxa-Michael/cyclobutanone ring-opening cascade to secure the alkyl citrate core, and asymmetric vinylzinc addition to form the C6 stereocenter. In addition, no oxidative adjustments are required to secure the citrate oxidation level.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Alcenos / Lactonas Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Austrália
Texto completo
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Alcenos / Lactonas Idioma: En Revista: Org Lett Assunto da revista: BIOQUIMICA Ano de publicação: 2019 Tipo de documento: Article País de afiliação: Austrália