Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines

Sandra Medina; Álvaro González-Gómez; Gema Domínguez; Javier Pérez-Castells

doi:10.1039/C2OB25755F

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Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines†

Sandra Medina,^a Álvaro González-Gómez,^a Gema Domínguez^a and Javier Pérez-Castells*^a

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* Corresponding authors

^a Universidad San Pablo-CEU, Departamento de Química, Facultad de Farmacia, Urb. Montepríncipe, 28668 Boadilla del Monte (Madrid), Spain
E-mail: jpercas@ceu.es

Abstract

2-Allyl-1-vinyl-β-carbolines and dihydropyrrolo-β-carbolines react with activated internal alkynes through novel rearrangement reactions leading to complex polycyclic structures. Favored reaction pathways depend on reaction conditions and on the presence of gold catalysts. In particular, upon reaction with 2 equiv. of the alkyne, new hexacyclic structures 10 are formed with total stereocontrol.

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DOI: https://doi.org/10.1039/C2OB25755F
Article type: Paper
Submitted: 19 Apr 2012
Accepted: 17 Jul 2012
First published: 20 Jul 2012

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Org. Biomol. Chem., 2012,10, 7167-7176

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Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines

S. Medina, Á. González-Gómez, G. Domínguez and J. Pérez-Castells, Org. Biomol. Chem., 2012, 10, 7167 DOI: 10.1039/C2OB25755F

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Organic & Biomolecular Chemistry

Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines†

Abstract

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Medium-sized and strained heterocycles from non-catalysed and gold-catalysed conversions of β-carbolines

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