Health & Environmental Research Online (HERO)


Print Feedback Export to File
6077700 
Journal Article 
A flexible and modular stereoselective synthesis of (9R,10S)-dihydrosterculic acid 
Palko, JW; Buist, PH; Manthorpe, JM 
2013 
1 
Tetrahedron: Asymmetry
ISSN: 0957-4166 
24 
4 
165-168 
WOS:000316167800001 
(9R,10S)-Dihydrosterculic acid has been prepared from (SS,SS)-1,1-bis(p-tolylsulfinyl)methane in a sequence involving an asymmetric Corey–Chaykovsky cyclopropanation and two sulfoxide/lithium exchange reactions. In most steps, the reaction conditions had to be optimized for the unbranched alkyl substituents, which were prone to Evans–Mislow rearrangements and subsequent degradation.