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  • Title: First total synthesis of 4-methylthio-3-butenyl glucosinolate.
    Author: Yamazoe S, Hasegawa K, Shigemori H.
    Journal: Biosci Biotechnol Biochem; 2009 Mar 23; 73(3):785-7. PubMed ID: 19270363.
    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.
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