First Enantioselective Total Synthesis of (−)-Centrolobine

The first enantioselective total synthesis of (−)-Centrolobine is described. The key reaction is the synthesis of the cis-disubstituted tetrahydropyran framework by intramolecular cyclization of the enantiopure hydroxyketone 3 with Et3SiH and TMSOTf. The stereoselective reduction of the β-ketosulfox...

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Bibliographic Details
Published in:Organic letters 2002-05, Vol.4 (10), p.1723-1725
Main Authors: Colobert, Françoise, Mazery, Renaud Des, Solladié, Guy, Carreño, M. Carmen
Format: Article
Language:English
Subjects:
Aldehydes
Cyclization
Indicators and Reagents
Magnetic Resonance Spectroscopy
Plants, Medicinal
Pyrans - chemical synthesis
Pyrans - chemistry
Spectrophotometry, Infrared
Stereoisomerism
Sulfoxides - chemistry
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Summary:The first enantioselective total synthesis of (−)-Centrolobine is described. The key reaction is the synthesis of the cis-disubstituted tetrahydropyran framework by intramolecular cyclization of the enantiopure hydroxyketone 3 with Et3SiH and TMSOTf. The stereoselective reduction of the β-ketosulfoxide 4 is the source of chirality. Revision of the absolute configuration of (−)-Centrolobine is proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol025778z