title: Bioinspired Synthesis of a Sedaxane Metabolite Using Catalytic Vanadyl Acetylacetonate and Molecular Oxygen.
abstract: A bioinspired synthesis of the sedaxane metabolite 2 from intermediate 3 using catalytic VO(acac)2 and O2 is described. Intermediate 3 was synthesized starting from 2-bromostyrene in four steps. The inner cyclopropyl ring of 3 was assembled with trans geometry using a highly diastereoselective Nishiyama cyclopropanation, and the outer hydroxycyclopropyl ring was installed using the Kulinkovich cyclopropanation. Additionally, conversion of 3 into 2 was demonstrated in in vitro microbial culture experiments consisting of bacteria and fungi.
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Sameer
authors.initials: S
authors.lastname: Tyagi
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Cook
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Dana A
authors.initials: DA
authors.lastname: DiDonato
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Jeffrey A
authors.initials: JA
authors.lastname: Key
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Bruce P
authors.initials: BP
authors.lastname: McKillican
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: William J
authors.initials: WJ
authors.lastname: Eberle
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: Timothy J
authors.initials: TJ
authors.lastname: Carlin
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection, LLC , 410 Swing Road, Greensboro, North Carolina 27409, United States.
authors.forename: David A
authors.initials: DA
authors.lastname: Hunt
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection , Jealott's Hill International Research Center, Bracknell, Berkshire, RG 42 6EY, United Kingdom.
authors.forename: Samantha J
authors.initials: SJ
authors.lastname: Marshall
authors.affiliation: Product Metabolism Analytical Sciences, Syngenta Crop Protection , Jealott's Hill International Research Center, Bracknell, Berkshire, RG 42 6EY, United Kingdom.
authors.forename: Nichola L
authors.initials: NL
authors.lastname: Bow
mesh_terms: D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry; D020058:Styrene / Q000737:chemistry
chemical_list: D000813:Anilides; D003521:Cyclopropanes; C583365:N-(2-(1,1'-bicyclopropyl)-2-ylphenyl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide; D011720:Pyrazoles; D020058:Styrene; D010100:Oxygen