First Enantioselective Total Synthesis of (−)-Centrolobine
- 17 April 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (10) , 1723-1725
- https://doi.org/10.1021/ol025778z
Abstract
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.Keywords
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