Issue 10, 2015

Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

Abstract

A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the creation of two/three new rings and three/four contiguous stereocentres, in which one of them is a tetra-substituted carbon center, in a highly diastereoselective fashion with excellent yields.

Graphical abstract: Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

Supplementary files

Article information

Article type
Communication
Submitted
16 Oct 2014
Accepted
05 Jan 2015
First published
05 Jan 2015

Org. Biomol. Chem., 2015,13, 2870-2874

Author version available

Highly regio- and diastereo-selective synthesis of novel tri- and tetra-cyclic perhydroquinoline architectures via an intramolecular [3 + 2] cycloaddition reaction

M. Bakthadoss, D. Kannan, J. Srinivasan and V. Vinayagam, Org. Biomol. Chem., 2015, 13, 2870 DOI: 10.1039/C4OB02203C

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