Use of dimethyldioxirane in the preparation of epoxy derivatives related to insect juvenile hormones

Angel Messeguer, Francisco Sánchez-Baeza, Josefina Casas, Bruce D. Hammock

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A study on the epoxidation of methyl farnesoate using the title reagent has been carried out. In addition, dimethyldioxirane has shown to be a convenient reagent for the synthesis of putative metabolites of juvenile hormone III, such as diepoxide 4, triepoxide 5 and epoxy diol 7. This reagent has also shown to be an excellent tool for performing the preparation of tritium labelled derivatives 4 and 7. Finally, molecular mechanics and NMR studies for the characterisation of cis and trans tetrahydrofuran derivatives 8a and 8b, compounds resulting from the acid or enzymatic hydrolysis of epoxy diol 7, are also reported.

Original languageEnglish (US)
Pages (from-to)1291-1302
Number of pages12
JournalTetrahedron
Volume47
Issue number7
DOIs
StatePublished - 1991

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Insect Hormones
Juvenile Hormones
Derivatives
Molecular mechanics
Enzymatic hydrolysis
Epoxidation
Tritium
Metabolites
Mechanics
Hydrolysis
Nuclear magnetic resonance
Acids
dimethyldioxirane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Use of dimethyldioxirane in the preparation of epoxy derivatives related to insect juvenile hormones. / Messeguer, Angel; Sánchez-Baeza, Francisco; Casas, Josefina; Hammock, Bruce D.

In: Tetrahedron, Vol. 47, No. 7, 1991, p. 1291-1302.

Research output: Contribution to journalArticle

Messeguer, Angel ; Sánchez-Baeza, Francisco ; Casas, Josefina ; Hammock, Bruce D. / Use of dimethyldioxirane in the preparation of epoxy derivatives related to insect juvenile hormones. In: Tetrahedron. 1991 ; Vol. 47, No. 7. pp. 1291-1302.
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