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Enantioselective total syntheses of nankakurines A and B: confirmation of structure and establishment of absolute configuration.
Nilsson, Bradley L; Overman, Larry E; Read de Alaniz, Javier; Rohde, Jason M.
Afiliación
  • Nilsson BL; Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, California 92697-2025, USA.
J Am Chem Soc ; 130(34): 11297-9, 2008 Aug 27.
Article en En | MEDLINE | ID: mdl-18680252
Total syntheses of (+)-nankakurine A (2) and (+)-nankakurine B (3) were accomplished by a sequence that employs an intramolecular dipolar cycloaddition of an azomethine imine intermediate to form the azatricyclic moiety and establish the relative configuration of the spiropiperidine ring. These syntheses, together with the synthesis of the originally purported structure 1 of nankakurine A, rigorously establish the relative and absolute configuration of these structurally unusual Lycopodium alkaloids. The syntheses are sufficiently concise that gram quantities of (+)-nankakurine A (2) and (+)-nankakurine B (3) will be available for further biological studies.
Asunto(s)

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Compuestos Heterocíclicos de Anillo en Puente / Lycopodium / Alcaloides Idioma: En Revista: J Am Chem Soc Año: 2008 Tipo del documento: Article País de afiliación: Estados Unidos

Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Asunto principal: Compuestos Heterocíclicos de Anillo en Puente / Lycopodium / Alcaloides Idioma: En Revista: J Am Chem Soc Año: 2008 Tipo del documento: Article País de afiliación: Estados Unidos