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Synthesis 1993; 1993(11): 1086-1088
DOI: 10.1055/s-1993-26005
short paper
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Convenient Isoprenylation of Aldehydes and Ketones: Synthesis of (±)-Ipsdienol and (±)-Ipsenol

Masao Tokuda* , Nobuo Mimura, Koichiro Yoshioka, Tamae Karasawa, Hirotake Fujita, Hiroshi Suginome
  • *Organic Synthesis Division, Department of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Sapporo 060, Japan
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Publication Date:
29 April 2002 (online)

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The reaction of 2-bromomethyl-1,4-dibromo-2-butene (1) with various aldehydes and ketones in tetrahydrofuran containing zinc powder under reflux gave the corresponding isoprenylated alcohols 3a-o in one step in good yields. The synthesis of ipsdienol (3e) and ipsenol (3c) was achieved by the present method starting from 3-methyl-2-butenal (2e) and isovaleraldehyde (2c).