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Whiting reaction
Chemical reaction
Chemical 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.
References
References
- Nayler, P.; Whiting, M. C. ''[[J. Chem. Soc.]]'' '''1954''', 4006–09.
- ''Synthesis of crystalline (.+-.)-fecapentaene'' Hans Rudolf Pfaendler, Franz Karl Maier, and Sonja Klar [[J. Am. Chem. Soc.]]; '''1986'''; 108(6) pp. 1338–39. ({{doi. 10.1021/ja00266a057)
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