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Title: Stereocontrolled annulations of indolo[2,3-a]quinolizidine-derived lactams with a silylated Nazarov reagent. Access to allo and epiallo yohimbine-type derivatives
Author: Arioli, Federica
Pérez Bosch, Maria
Are, Celeste
Estarellas, Carolina
Luque Garriga, F. Xavier
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Lactames
Química orgànica
Organic chemistry
Issue Date: 14-Sep-2015
Publisher: Wiley-VCH
Abstract: The facial selectivity of double Michael addition reactions of the silylated Nazarov reagent 4 to unsaturated indolo[2,3-a]quinolizidine lactams 3 has been studied. Pentacyclic 3-H/15-H trans adducts 5 are generated from Nind -unsubstituted lactams, but the corresponding cis isomers 6 are formed when the indole nitrogen has a tert-butyloxycarbonyl (Boc) substituent. This reversal in the facial selectivity of the annulation has been rationalized by means of theoretical calculations, which indicate that the initial nucleophilic attack under stereoelectronic control is hampered by the presence of the bulky Boc group. The synthetic usefulness of the pentacyclic Nazarov-derived adducts is demonstrated by their conversion into allo and epiallo yohimbine-type targets.
Note: Versió postprint del document publicat a:
It is part of: Chemistry-A European Journal, 2015, vol. 21, num. 38, p. 13382-13389
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ISSN: 0947-6539
Appears in Collections:Articles publicats en revistes (Nutrició, Ciències de l'Alimentació i Gastronomia)
Articles publicats en revistes (Institut de Biomedicina (IBUB))
Articles publicats en revistes (Farmàcia, Tecnologia Farmacèutica i Fisicoquímica)

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