• Bulletin of the Korean Chemical Society
• /
• 제22권12호
• /
• pp.1390-1392
• /
• 2001

• Bulletin of the Korean Chemical Society
• /
• 제29권12호
• /
• pp.2513-2516
• /
• 2008

• Bulletin of the Korean Chemical Society
• /
• 제32권spc8호
• /
• pp.3137-3140
• /
• 2011

• Bulletin of the Korean Chemical Society
• /
• 제10권5호
• /
• pp.482-483
• /
• 1989

• Bulletin of the Korean Chemical Society
• /
• 제9권6호
• /
• pp.379-381
• /
• 1988

Racemic nuciferal(1) and nuciferol(2), the terpenic natural perfumeries, have been synthesized by a simple procedure. The benzylic halide 6; 1-(1-chloroethyl)-4-methylbenzene, was prepared by converting p-tolualdehyde(4) into 1-(p-tolyl)-1-ethanol(5), followed by convertion of 5 into corresponding chloride. The Grignard reagent of 6 was reacted with the bromoacetal 7, 2-(2-bromoethyl)-1,3-dioxolane, to give a crosscoupling product 8, which was hydrolysed to 4-(p-tolyl)-pentanal (9). The Wittig reaction of isopropylide 10 with 9 yielded arcurcumen(11). The stereospecific allylic oxidation of the gem-dimethyl olefin 11 with selenium dioxide afforded a trans-aldehyde, (${\pm}$)-1, which was reduced to corresponding alcohol, (${\pm}$)-2.