Issue 4, 2016

Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24

Abstract

In contrast to a biomimetic electrophilic cyclisation cascade, we employ a contra-biomimetic nucleophilic cyclisation cascade to give the tricyclic core of 4-hydroxy-GR24 in a single step. Kinetic resolution using a stereoselective Noyori transfer hydrogenation enables the concise synthesis of any enantiomerically enriched 4-hydroxy-GR24 stereoisomer.

Graphical abstract: Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24

Supplementary files

Article information

Article type
Communication
Submitted
16 Nov 2015
Accepted
14 Dec 2015
First published
15 Dec 2015

Org. Biomol. Chem., 2016,14, 1236-1238

Author version available

Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24

J. C. Morris and C. S. P. McErlean, Org. Biomol. Chem., 2016, 14, 1236 DOI: 10.1039/C5OB02349A

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