Journal
HETEROCYCLES
Volume 97, Issue 2, Pages 1191-1202Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-18-S(T)66
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Funding
- Ministerio de Ciencia e Innovacion (MCINN) [CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165]
- Ministerio de Economia Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC CTQ2016-81797-REDC, CTQ2017-85093-P]
- FEDER
- Generalitat Valencian [PROMETEOII/2014/017]
- University of Alicante
- Ministere de l'Enseignement Superieur et de la Recherche Scientifique Algerienne
- Direction de la Cooperation et des Echanges Interuniversitaires Programme de Formation Residentielle a l'Etranger au titre de l'annee universitaire 2016/2017 Programme National Exceptionnel (PNE)
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The total synthesis of (+)-C(9a)-epiepiquinamide has been achieved starting from ethyl 5-bromopentanoate, (Rs)-tert-butanesulfinamide, nitromethane, ethyl acrylate and acetic anhydride. The diastereoselective coupling of ethyl 4-nitrobutanoate and a chiral N-tert-butanesulfinyl imine, along with a double cyclization involving a primary amine through an intramolecular N-alkylation and lactam formation, are key steps of this synthesis.
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