Whiting reaction explained

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

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.

Notes and References

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.