Family Guy Presents: 118 to 119

Evil Monkey!

The evil monkey and angry chicken were snooping around, checking out what Stewie and Overman had presented. They saw that Stewie and Overman had referenced an interesting article concerning ring-closing methathesis by a guy named Wipf:

Wipf, P.; Rector, S. R.; Takahasi, H. J. Am. Chem. Soc. 2002, 124, 14848-14849.

Overman's transformation of molecule 118 into 119 is a ring-closing metathesis that uses the second iteration of Grubbs’ catalyst as the principle reagent. The article cited here references an earlier experiment in which one of the highlights is a ring-closing metathesis reaction using a similar ruthenium-based reagent.

After seeing this, the dasterly duo of evil monkey and chicken decided to investigate this reference in the Science Citation Index to get a better idea on what Stewie and Overman were up to.

First, they noticed this article by Mardsen:

Mardsen, S. P.; McElhinney A.D. Beilstein J. Org. Chem. 2008, 4, 5397-5408.

Mardsen Reaction Scheme

Here, the second iteration of Grubbs’ catalyst, as in the transformation between molecules 118 and 119, is employed to allow for ring closing-metathesis.

Next, the two came across this article by Arisawa:

Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. Chem. Rec. 2007, 7, 238-253.

art2chem

Here, the first generation of Grubbs’ catalyst is used to allow for a ring-closing metathesis.

Last, the monkey and chicken found this article by Barberis:

Barberis, M.; Garcia-Losada, P.; Pleite, S.; Rodriguez J. R.; Sorian, J. F.; Mendiola J. Tetrahedron Lett. 2005, 46, 4847-4850.

art3chem

Here, an azepine ring undergoes ring-closing metathesis as seen in the Wipf article cited by Overman (and Stewie).