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Stereochemical Dichotomy in Two Competing Cascade Processes: Total Syntheses of Both Enantiomers of Spiroxin A.
Ando, Yoshio; Tanaka, Daisuke; Sasaki, Ryota; Ohmori, Ken; Suzuki, Keisuke.
Afiliación
  • Ando Y; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro, Tokyo, 152-8551, Japan.
  • Tanaka D; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro, Tokyo, 152-8551, Japan.
  • Sasaki R; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro, Tokyo, 152-8551, Japan.
  • Ohmori K; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro, Tokyo, 152-8551, Japan.
  • Suzuki K; Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro, Tokyo, 152-8551, Japan.
Angew Chem Int Ed Engl ; 58(36): 12507-12513, 2019 09 02.
Article en En | MEDLINE | ID: mdl-31278822
ABSTRACT
The first total synthesis of the marine antibiotic spiroxin A has been achieved for both enantiomeric forms. The discovery of two competing cascade processes triggered by two orthogonal stimuli, photo-irradiation or acid/base treatment, enabled the divergent conversion of a single chiral, nonracemic bis-quinone into both enantiomers of an advanced intermediate en route to both (-)- and (+)-spiroxin A. The mechanism of the enantiodivergence is discussed.
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Compuestos de Espiro / Naftalenos Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: Japón
Texto completo
Imprimir
XML
PubMed Links
Buscar en Google

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Compuestos de Espiro / Naftalenos Idioma: En Revista: Angew Chem Int Ed Engl Año: 2019 Tipo del documento: Article País de afiliación: Japón