Whiting reaction
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The Whiting reaction is an organic reaction converting a propargyl diol into a diene with 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
