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 language | English (US) |
|---|---|
| Pages (from-to) | 1291-1302 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 47 |
| Issue number | 7 |
| DOIs | |
| State | Published - 1991 |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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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 journal › Article
}
TY - JOUR
T1 - Use of dimethyldioxirane in the preparation of epoxy derivatives related to insect juvenile hormones
AU - Messeguer, Angel
AU - Sánchez-Baeza, Francisco
AU - Casas, Josefina
AU - Hammock, Bruce D.
PY - 1991
Y1 - 1991
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0026031691&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0026031691&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)86386-9
DO - 10.1016/S0040-4020(01)86386-9
M3 - Article
VL - 47
SP - 1291
EP - 1302
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 7
ER -