Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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A Total Synthesis of Nuciferal and Nuciferol

  • Lee, Woo-Young (Department of Chemistry, Seoul National University) ;
  • Lee, Youn-Young (Department of Chemistry, Seoul National University) ;
  • Lim, Kwang-Su (Department of Chemistry, Seoul National University) ;
  • Goo, Yang-Mo (Department of Pharmacy, Seoul National University) ;
  • Park, Oee-Sook (Department of Chemistry, Chungbuk National University)
  • Published : 1988.12.20
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Abstract

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.

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References

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  1. ChemInform Abstract: A Total Synthesis of Nuciferal and Nuciferol. vol.20, pp.21, 1988, https://doi.org/10.1002/chin.198921283