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Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.
Scheerer, Jonathan R; Leeth, Ella B; Sprow, Jennifer A.
Afiliação
  • Scheerer JR; Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
  • Leeth EB; Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
  • Sprow JA; Department of Chemistry, William & Mary, P.O. Box 8795, Williamsburg, VA 23187, USA.
Synthesis (Stuttg) ; 55(15): 2319-2324, 2023 Aug.
Article em En | MEDLINE | ID: mdl-37691879
A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of ß-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (-)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2023 Tipo de documento: Article