title: Modification of the butenyl-spinosyns utilizing cross-metathesis.
abstract: The discovery of a strain of Saccharopolyspora sp. that produced a number of spinosyn analogs that had not before been seen gave an ideal opportunity for extending our knowledge of that SAR of these highly efficacious insecticides. In particular, these compounds contained a butenyl group connected to C-21 which in the regular spinosyns was substituted with a simple ethyl group. The double bond therefore gave us a handle to further modify this position allowing us to substitute different groups there. In this paper we show one of our approaches to this modification using olefin cross-metathesis. Even though the spinosyns were not highly efficient substrates for metathesis reactions, we were nevertheless successful in extending their chemistry accordingly.
authors.affiliation: Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN 46268, United States.
authors.forename: John
authors.initials: J
authors.lastname: Daeuble
authors.forename: Thomas C
authors.initials: TC
authors.lastname: Sparks
authors.forename: Peter
authors.initials: P
authors.lastname: Johnson
authors.forename: Paul R
authors.initials: PR
authors.lastname: Graupner
mesh_terms: D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D016930:Saccharopolyspora / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D018942:Macrolides