Total Synthesis of the Racemic Form of the Second Juvenile Hormone (Methyl 12-Homojuvenate) from the Cecropia Silk Moth

Total Synthesis of the Racemic Form of the Second Juvenile Hormone (Methyl 12-Homojuvenate) from the Cecropia Silk Moth

Methyl cis-10-epoxy-3, 7, 11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-γ -bromo-β ,β -dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hor...

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Veröffentlicht in:Proceedings of the National Academy of Sciences - PNAS 1969-04, Vol.62 (4), p.1005-1009
Hauptverfasser: Johnson, William S., Campbell, Simon F., Krishnakumaran, A., Meyer, Andre S.
Format: Artikel
Sprache:eng
Schlagworte:
Bromides
Esters
Ethers
Hormones
Isomers
Juvenile hormones
Ketones
Moths
Physical Sciences: Chemistry
Pupae
Silkworms
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Zusammenfassung:Methyl cis-10-epoxy-3, 7, 11-trimethyl-trans,trans-2,6-tridecadienoate has been stereoselectively synthesized in 12 steps starting from methyl trans-γ -bromo-β ,β -dimethylacrylate and 1-acetyl-1-methylcyclopropane. The final product proved to be identical with the second, less abundant juvenile hormone (methyl 12-homojuvenate) isolated from the Cecropia silk moth. The biological activities of the compound were evaluated in various insects.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.62.4.1005