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Chemistry. 2010 Feb 22;16(8):2487-95. doi: 10.1002/chem.200902774.

(+)-(R,Z)-5-Muscenone and (-)-(R)-muscone by enantioselective aldol reaction and Grob fragmentation.

Author information

1
Firmenich SA, Corporate R&D Division, P.O. Box 239, 1211 Geneva 8, Switzerland. charles.fehr@firmenich.com

Abstract

(+)-(R,Z)-5-Muscenone ((R)-1) was synthesized by an enantioselective aldol reaction, catalyzed by new ephedrine-type Ti reagents (up to 70 % enantiomeric excess). Substrate-directed diastereoselective reduction of the aldol product and Grob fragmentation of the tosylate of the resultant 1,3-diol afforded (+)-1. This approach also gave access to (-)-(R,E)-5-muscenone and (-)-(R)-muscone.

PMID:
20077541
DOI:
10.1002/chem.200902774

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