First total synthesis of 4-methylthio-3-butenyl glucosinolate.
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.
Yamazoe
Sayumi
S
Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Japan.
Hasegawa
Koji
K
Shigemori
Hideyuki
H
D005961:Glucosinolates / Q000138:chemical synthesis* / Q000737:chemistry; D031224:Raphanus / Q000737:chemistry; D013237:Stereoisomerism
C507366:4-methylthio-3-butenyl glucosinolate; D005961:Glucosinolates