Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 4/7/2002
Publication Date: N/A
Technical Abstract: Racemic (Z)-9-octadecen-4-olide was prepared by a samarium iodide mediated coupling of (Z)-6-pentadecenal with ethyl-3-bromopropionate. A chiral synthesis of (R,Z)-9-octadecen-4-olide was accomplished by a Grignard coupling of (Z)-1-bromotridec-4-ene with (S)-(-)-methyl-4,5-epoxypentanoate. The chiral epoxide was prepared in several steps from L-glutamic acid. The synthesis of butanolides via alkyl-1,4-diols will also be presented.