Whiting_reaction

Whiting reaction

Whiting reaction

Chemical reaction

The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride.[1]

Whiting reaction

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

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

References

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