Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24. Issue 4 (21st December 2015)

• Record Type: Journal Article
• Authors: Morris, J. C.; McErlean, C. S. P.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 4(2016)
• Page Start: 1236
• Page End: 1238
• Publication Date: 2015-12-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02349a
• Languages: English
• ISSNs: 1477-0520

Abstract

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. 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.