Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Communications
First Total Synthesis of 4-Methylthio-3-butenyl Glucosinolate
Sayumi YAMAZOEKoji HASEGAWAHideyuki SHIGEMORI
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2009 年 73 巻 3 号 p. 785-787

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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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© 2009 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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