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Synthesis of a mixture of (±)-dehydrojuvabione and its stereoisomer

✍ Scribed by Kenji Mori; Masanao Matsui

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
159 KB
Volume
8
Category
Article
ISSN
0040-4039

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✦ Synopsis

Dehydrojurebiane (I) is e compound with high juvenile hormone activity isolated from Csaohoslorek balsam fir (Abies bels8mee L.) by sorm and his co-workers (1). After the completion of the synthesis of (*)-juvabione (II) (2), e congener of dehydrojuvabione (l)(3), we turned our attention to the synthesis of this sesquiterpene ester which has now been accomplished. S-(p-Methoxyphenyl)butyryl chloride (IIIa)(2) was condensed with &ethyl ethoxymegnesiomslonete to give an ester (IIIb)(4), which was hydrolysed end decerboxylated to give e ketone (IIIc), b.p. 94-95°/0.15mm, ns41.5104; 2,4dinitrophenylhydrasone, m.p. 109-111'. Cerbethoxyletion of the ketone (111~) with diethyl carbonate end sodium smide gsve a S-keto ester (IIId), b.p. 130-132°/0.1mm, ni51.504S.

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