References

Source 8 is referenced:
Burns, N. Z.; Baran, P. S. Angew. Chem., Int. Ed. 2007, 46, 205–208

The following sources reference source 8:

1. Burns, N. Z.; Jessing, M.; Baran, P. S. Tetrahedron. 2009, 65, 6600-6610.
2. Burns, N. Z.; Krylova, I.N.; Hannoush, R. N.; Baran, P. S. J. Am. Chem. Soc. 2009, 131,
9172.
3. Taniguchi, T.; Zaimoku, H.; Ishibashi, H. J. Am. Chem. Soc. 2009, 74, 2624-2626.
4. Furstner, A.; Ackerstaff, J. Chem. Commun. 2008, 25, 2870-2872.

In depth look at source 1:

Burns, N. Z.; Jessing, M.; Baran, P. S. Tetrahedron. 2009, 65, 6600-6610.

Step 72-73:

The article traces the effort toward the indeno-tetra-hydrapyridine of haouamine A. Haouamine A is part of a class of natural products that originate in southern Spain. It has shown to have powerful and selective cytotoxic activity against HT-29 human colon cancer. TEMPO/NaOCl oxidation was the only way found to oxidize the diol especially because this diol was very susceptible to oxidative glycol cleavage. NaOCl/TEMPO oxidation produced an alpha-hydroxy ketone with high yield (96%). It also maintained the stereochemistry of the molecule. The discovery that TEMPO oxidation was the only one to produce the desired product is an intriguing discovery that has placed scientists one step closer to uncovering the mystery behind the indeno-tetra-hydropyridine core of haouamine A.

SPANAKOPITA (Greek Spinach Pie)

Ingredients:

3 tablespoons olive oil

1 large onion

1bunch of scallions

2 cloves of minced garlic

2 pounds of chopped spinach

1/2 cup fresh parsley

2 eggs

1/2 cup ricotta cheese

1 cup feta cheese

8 sheets phyllo dough

1/4 cup olive oil

Taniguchi, T.; Zaimoku, H.; Ishibashi, H. J. Am. Chem. Soc. 2009, 74, 2624-2626.

This article discusses the construction of indeno-tetra-hydropyridine 14, which is the intermediate for the synthesis of haouamine A. As previously noted, haouamines are class of cytotoxic compounds found in natural marine products off the coast of southern Spain, and they have proven to have selective cytotoxic activity against human colon cancer. This article elaborates on the work from “source 1” (above) and the original source 8. This article discusses a new way to form the haouamine A intermediate for the synthesis haouamine A as discussed in the previous sources. Instead of using TEMPO and NaOCl for the critical step, the new method discussed by this source discusses the use of an “intramolecular cascade Mizoroki-Heck: reaction” as the critical step for the synthesis of indeno-tetra-hydropyridine.

Directions:

1. Preheat oven to 350˚F. Lightly oil a 9x9in square pan

2. Heat olive oil in a large pan over medium heat. Saute onion, green onions, and garlic until lightly browned. Stir in spinach and parsley until spinach in limp (~2min). Remove from heat and let cool.

3. Mix eggs, ricotta, feta in large bowl. Stir in spinach mixture. Lay one sheet of phyllo dough in a prepared baking pan, and brush lightly with olive oil. Repeat this three more times. Sheets will overlap the pan. Spread spinach and cheese mixture into pan and fold overhanging dough over filling. If you're up to the challenge, try making individual triangles rather than one giant square.) Brush with oil to seal.

4. Bake in preheated oven for 30-40 min until golden brown.

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