Whiting reaction

The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.



This organic reduction has been applied in the synthesis of fecapentaene, a suspected cause of colon cancer:
 * [[Image:WhitingReaction.png|center|500px|alt=SMILES-esque: thp is CC1CCCCO1, tbdms is CSi(C)(C)C(C)(C)C. Step 1 is CCC=CC=CC(Othp)C#CC(O)C=COCC(Otbdms)COtbdms, to which is added LiAlH4 in THF to obtain Step 2, namely CCC=CC=CC=CC=CC=COCC(Otbdms)COtbdms, to which is added nBu4NF in THF/Et2O to obtain Step 3, namely CCC=CC=CC=CC=CC=COCC(O)CO]]

Protecting groups are tetrahydropyranyl and TBSMS; the final step is deprotection with tetra-n-butylammonium fluoride.