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

• Published in: Ultrasonics 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
• Language: English
• 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

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.