Stereocontrolled SPOS of an Indoline-Alkaloid-like Library

Z. Gan; P. T. Reddy; S. Quevillon; S. Couve-Bonnaire; P. Arya

doi:10.1055/s-2005-865381

Synfacts, Table of Contents

Synfacts 2005(0): 0077-0077
DOI: 10.1055/s-2005-865381

Polymer-Supported Synthesis

Stereocontrolled SPOS of an Indoline-Alkaloid-like Library

Contributor(s): Yasuhiro Uozumi, Masahiro Kimura

Z. Gan, P. T. Reddy, S. Quevillon, S. Couve-Bonnaire, P. Arya*
National Research Council of Canada, University of Ottawa, Canada
Stereocontrolled Solid-Phase Synthesis of a 90-Membered Library of Indoline-Alkaloid-like Polycycles from an Enantioenriched Aminoindoline Scaffold
Angew. Chem. Int. Ed. 2005, 44: 1366-1368

Abstract

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Key words

combinatorial chemistry - cyclization - indoline alkaloids - protecting groups - solid-phase

Significance

A 90-membered library of indoline-alkaloid-like polycyclic compounds was synthesized through stereoselective hetero-Michael reactions with nitrogen nucleophiles as the key step. The seven synthetic steps on the solid-support were carried out under very mild conditions to give the library members in high yields (80-85%).

Comment

Solid-phase synthesis is an effective tool to prepare libraries of drug candidates in a high-throughput manner. The present method can easily introduce the four diversity sites into an indoline-alkaloid-like tricyclic backbone by employing mild conditions, which are appropriate to explore and generate a molecule library.

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