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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Crop Bioprotection Research » Research » Publications at this Location » Publication #133650
Title: SYNTHESIS OF (Z)-9-OCTADECEN-4-OLIDE, A FEMALE-PRODUCED PHEROMONE OF THE CURRANT STEM GIRDLER (A SAWFLY, HYMENOPTERA:CEPHIDAE)

Author
item Petroski, Richard

Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 4/7/2002
Publication Date: N/A
Citation: N/A

Interpretive Summary:

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.