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Title: Origin of the Base-Dependent Facial Selectivity in Annulation Reactions of Nazarov-Type Reagents with Unsaturated Indolo[2,3-a] quinolizidine Lactams
Author: Estarellas, Carolina
Arioli, Federica
Pérez Bosch, Maria
Are, Celeste
Hevia, David
Molins i Grau, Elies
Luque Garriga, F. Xavier
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Teoria del funcional de densitat
Indicadors (Química)
Proves i reactius químics
Química orgànica
Density functionals
Indicators and test-papers
Chemical tests and reagents
Organic chemistry
Issue Date: 25-Jul-2017
Publisher: Wiley-VCH
Abstract: Methyl-substituted Nazarov reagent 4 reacts stereoselectively with N-ind-Boc indoloquinolizidine lactams to give the expected 3-H/15-H cis pentacyclic yohimbine-type adducts when using 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) as the base. However, a dramatic change of the facial selectivity was observed when the reaction was performed in the presence of Cs2CO3, leading to the corresponding trans adducts. This annulation is the key step of a stereocontrolled synthesis of the 17acarba analogue of the heteroyohimbine alkaloid akuammigine. Theoretical calculations were used to rationalize the facial selectivity of these double Michael addition reactions.
Note: Versió postprint del document publicat a:
It is part of: European Journal of Organic Chemistry, 2017, num. 27, p. 3969-3979
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ISSN: 1434-193X
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)

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