First total synthesis of 4-methylthio-3-butenyl glucosinolate

Biosci Biotechnol Biochem. 2009 Mar 23;73(3):785-7. doi: 10.1271/bbb.80862. Epub 2009 Mar 7.

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.

MeSH terms

  • Glucosinolates / chemical synthesis*
  • Glucosinolates / chemistry
  • Raphanus / chemistry
  • Stereoisomerism

Substances

  • 4-methylthio-3-butenyl glucosinolate
  • Glucosinolates