Synthesis of highly -enriched stereoisomers of hydroxy-GR24

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 e...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2016-01, Vol.14 (4), p.1236-1238
Main Authors: Morris, J. C, McErlean, C. S. P
Format: Article
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Summary: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. 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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob02349a