Efficient synthesis of (±)-7-isopropyl-2,10-dimethyl-8(E),10-undecadien-4-one and 3,7-dimethyl-11-oxo-2(E),6(E)-dodecadienol (oxocrinol) under ultrasound

A simple and convergent synthesis of the title compounds has been achieved involving Zn–Cu couple catalysed conjugate addition of allylic halides to α,β-unsaturated carbonyl compounds promoted by ultrasonic waves in aqueous medium as a key step in good overall yields.

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Bibliographic Details
Published inUltrasonics sonochemistry Vol. 8; no. 2; pp. 123 - 126
Main Authors Kad, G.L., Singh, Vasundhara, Chaudhary, Sangeeta, Setia, Sushma, Bhandari, Monica, Singh, Jasvinder
Format Journal Article
LanguageEnglish
Published Netherlands Elsevier B.V 01.04.2001
Subjects
(±)-7-isopropyl-2,10-dimethyl-8(E),10-undecadien-4-one
3,7-dimethyl-11-oxo-2(E),6(E)-dodecadienol (oxocrinol)
Indicators and Reagents
Ketones - chemistry
Magnetic Resonance Spectroscopy
Nicotiana - chemistry
Plants, Toxic
Synthesis
Terpenes - chemistry
Terpenoid
Ultrasonics
Ultrasound
(±)-7-isopropyl-2,10-dimethyl-8(E),10-undecadien-4-one
Terpenoid
Synthesis
3,7-dimethyl-11-oxo-2(E),6(E)-dodecadienol (oxocrinol)
Ultrasound
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Summary:A simple and convergent synthesis of the title compounds has been achieved involving Zn–Cu couple catalysed conjugate addition of allylic halides to α,β-unsaturated carbonyl compounds promoted by ultrasonic waves in aqueous medium as a key step in good overall yields.
ISSN:1350-4177
1873-2828
DOI:10.1016/S1350-4177(00)00063-8