Whiting reaction
From Wikipedia, the free encyclopedia
The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.[1]
This organic reduction has been applied in the synthesis of facapentadiene.[2][3][4]
[edit] References
- ^ Nayler, P.; Whiting, M. C. J. Chem. Soc. 1954, 4006-4009.
- ^ Synthesis of crystalline (.+-.)-fecapentaene Hans Rudolf Pfaendler, Franz Karl Maier, and Sonja Klar J. Am. Chem. Soc.; 1986; 108(6) pp 1338 - 1339. (doi:10.1021/ja00266a057)
- ^ a mutagenic glyceryl ether lipid which can occur in trace amounts in the feces of people living in industrialized countries and are suspected to be a cause for colon cancer
- ^ protecting groups are tetrahydropyranyl and TBSMS, the final step is deprotection with tetra-n-butylammonium fluoride
