CITATIONS:

The following three articles were cited in the reference concerning this reaction and the following reactions used in this synthesis:

1. Luche, J.L. J. Am. Chem. Soc. 1978, 100, 2226-2227.

2. O'Malley, D.P.; Li, K.; Maue, M.; Zografos, A.L.; Baran, P.S. J. Am. Chem. Soc. 2007, 129, 4762-4775.

3. Sivappa, R.; Hernandez, N.M.; He, Y.; Lovely, C. J. Org. Lett. 2007, 9, 3861-3864.

The publication by Dr. Luche in the 1978 Journal of the American Chemical Society outlines a process by which conjugated ketones are treated with sodium borohydride in the presence of alcohol and a lanthanoid. The combination of reagents results in a 1,2 reduction of the ketone, creating an alcohol in its place. This reaction is carried out with great speed and with high yields, taking place in the space of 5-10 minutes. The mechanism of the reaction has not been studied in depth, but several propositions have been made. One is that the lanthanoid in the reaction forms a lanthanoid borohydride, which in turn reduces the ketone. Another proposition is that a complex forms between the carbonyl compound and the rare earth metal of the lanthanoid. Neither possibility can be discredited by the data gathered in the journal. The findings of this journal have been cited in over 800 other journals since its publication.

This paper was referenced for the reaction following the synthesis of Compound 6. The following diagram outlines this reaction:

This article was also reference by the following three papers:

1. Hayashi, N.; Suzuki, T.; Usui, K. Tetrahedron. 2009, 65, 888-895.
*This article describes the creation of the compound (+)-phomopsidin, an inhibitor to the
assembly of microtubule proteins, the synthesis of which can be carried out using an
intermediate formed from a Luche reduction.

2. Cavezza, A.; Boulle, C.; Gueguiniat, A. Bioorg. Med. Chem. Lett. 2009, 19, 845-849.
*The Luche reduction was used in this article to perform the reduction of an unconjugated
ketone, as part of the synthesis of a commercial compound called Pro-XylaneTM.

3. Murphy, A.C.; Devenish, S.R.A.; Muscroft-Taylor, A.C.; Blunt, J.W.; Munro, M.H.G. Org. Biomol. Chem. 2008, 6, 3854-3862.
*The Luche reduction was used in this article to successfully reduce an enone to an allylic
alcohol.