Whiting reaction

Whiting reaction

The Whiting reaction is an organic reaction converting a propargyl diol into a diene using lithium aluminium hydride. [Nayler, P.; Whiting, M. C. "J. Chem. Soc." 1954, 4006-4009.]

This organic reduction has been applied in the synthesis of "facapentadiene". ["Synthesis of crystalline (.+-.)-fecapentaene" Hans Rudolf Pfaendler, Franz Karl Maier, and Sonja Klar J. Am. Chem. Soc.; 1986; 108(6) pp 1338 - 1339. (DOI|10.1021/ja00266a057)] [a mutagenic glyceryl ether lipid which can occur in trace amounts in the feces of people living in industrialized countries and are suspected to be a cause for colon cancer] [protecting groups are tetrahydropyranyl and TBSMS, the final step is deprotection with tetra-n-butylammonium fluoride]

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