title: First total synthesis of 4-methylthio-3-butenyl glucosinolate.
abstract: The first total synthesis of 4-methylthio-3-butenyl glucosinolate (MTBG), a natural bioactive compound and a precursor of radish phototropism-regulating substances, was achieved from commercially available 1,4-butanediol. The glucosinolate framework was prepared by coupling of an oximyl chloride derivative and tetraacetyl thioglucose. A methylthio group was introduced to the framework by a Wittig reaction between triphenylphosphonium thiomethylmethylide and an aldehyde intermediate of glucosinolate. The synthetic route should facilitate preparation of various derivatives needed for probe synthesis based on MTBG.
authors.affiliation: Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Japan.
authors.forename: Sayumi
authors.initials: S
authors.lastname: Yamazoe
authors.forename: Koji
authors.initials: K
authors.lastname: Hasegawa
authors.forename: Hideyuki
authors.initials: H
authors.lastname: Shigemori
mesh_terms: D005961:Glucosinolates / Q000138:chemical synthesis* / Q000737:chemistry; D031224:Raphanus / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C507366:4-methylthio-3-butenyl glucosinolate; D005961:Glucosinolates