Synthesis and odor of optically active rose oxide

✍ Scribed by Takeshi Yamamoto; Hiroyuki Matsuda; Yasuhide Utsumi; Toshimitsu Hagiwara; Tsuneyoshi Kanisawa

• Book ID: 104252459
• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 395 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02311-0

✦ Synopsis

Stereoselective synthesis of optically active rose oxide (1) by KHSO 4 and Pd-BINAP-catalyzed cyclization of (3R)-and (3S)-3,7-dimethyl-6,7-octadien-1-ol ( 5) is described. One-pot synthesis of the (3R)-and (3S)-allenyl alcohol 5 from (3R)-and (3S)-citronellol (2) (98% ee) is also described. Furthermore, the odor properties of the four diastereomers of 1 are reported.