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Stereochemical Definition of the Natural Product (6R,10R,13R, 14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-Azaspiracid-3 by Total Synthesis and Comparative Analyses.
Kenton, Nathaniel T; Adu-Ampratwum, Daniel; Okumu, Antony A; McCarron, Pearse; Kilcoyne, Jane; Rise, Frode; Wilkins, Alistair L; Miles, Christopher O; Forsyth, Craig J.
Afiliação
  • Kenton NT; Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH, 43210, USA.
  • Adu-Ampratwum D; Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH, 43210, USA.
  • Okumu AA; Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Ave, Columbus, OH, 43210, USA.
  • McCarron P; Measurement Science and Standards, National Research Council of Canada, 1411 Oxford St., Halifax, Nova Scotia, B3H 3Z1, Canada.
  • Kilcoyne J; Marine Institute, Rinville, Oranmore, Co., Galway, Ireland.
  • Rise F; Department of Chemistry, University of Oslo, 0315, Oslo, Norway.
  • Wilkins AL; Norwegian Veterinary Institute, P.O. Box 750 Sentrum, 0106, Oslo, Norway.
  • Miles CO; Chemistry Department, University of Waikato, Private Bag 3105, 3240, Hamilton, New Zealand.
  • Forsyth CJ; Measurement Science and Standards, National Research Council of Canada, 1411 Oxford St., Halifax, Nova Scotia, B3H 3Z1, Canada.
Angew Chem Int Ed Engl ; 57(3): 810-813, 2018 01 15.
Article em En | MEDLINE | ID: mdl-29193497
ABSTRACT
The previously accepted structure of the marine toxin azaspiracid-3 is revised based upon an original convergent and stereoselective total synthesis of the natural product. The development of a structural revision hypothesis, its testing, and corroboration are reported. Synthetic (6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R, 33R,34R,36S,37S,39R)-azaspiracid-3 chromatographically and spectroscopically matched naturally occurring azaspiracid-3, whereas the previously assigned 20R epimer did not.
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Texto completo: 1 Bases de dados: MEDLINE Assunto principal: Piranos / Produtos Biológicos / Furanos Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Estados Unidos
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Bases de dados: MEDLINE Assunto principal: Piranos / Produtos Biológicos / Furanos Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Estados Unidos