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Whiting reaction

From Wikipedia, the free encyclopedia
Chemical reaction

TheWhiting reaction is anorganic reaction converting apropargyldiol into adiene usinglithium aluminium hydride.[1]

Whiting reaction
Whiting reaction

Thisorganic reduction has been applied in the synthesis offecapentaene, a suspected cause ofcolon 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 aretetrahydropyranyl andTBSMS; the final step is deprotection withtetra-n-butylammonium fluoride.

References

[edit]
  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 KlarJ. Am. Chem. Soc.;1986; 108(6) pp. 1338–39. (doi:10.1021/ja00266a057)
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