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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]

Whiting reaction
Whiting reaction

This organic reduction has been applied in the synthesis of fecapentaene, a suspected cause of colon cancer:[2]

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

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  1. ^ Nayler, P.; Whiting, M. C. J. Chem. Soc. 1954, 4006–09.
  2. ^ 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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