CHEMISTRY 2320 – ADVANCED ORGANIC CHEMISTRY 2

Journal Club

Guidelines for Journal Club presentations:
 • Select a current (2007) paper of eminent interest and/or of general high significance for the field of synthetic organic chemistry.
 • The reference for this paper has to be publicized to the class by email at least 1 week (7 days) before the meeting. No handouts are required.
 • Since everybody should be familiar with the content of the paper, the following questions should be addressed in the presentation:
   - What is the key innovative aspect of this work?
   - How does it relate to the state-of-the-art in the field?
   - What are the possible future extensions of this work?
 • Presentations should be planned for ca. 15 min; a copy (pdf) will be posted on this web site. 

Good resources to quickly identify suitable papers are Methods in Organic Synthesis (MOS) and Synfacts.

Sample Presentation: Enantioselective Organo-Cascade Catalysis [view]

1/8: P. Wipf: Lowe, Jason T.; Wrona, Iwona E.; Panek, James S. Total Synthesis of Bistramide A. Organic Letters ACS ASAP. (pdf)

1/22: A.-H. Yeh: Second Generation Catalytic Asymmetric Synthesis of Tamiflu: Allylic Substitution Route; Mita, T.; Fukuda, N.; Roca, F. X.; Kanai, M.; Shibasaki, M. Org. Lett. 2006; ASAP Article; DOI: 10.1021/ol062663c. (pdf) (pdf of presentation).

1/22: S. Osman: Total Synthesis of Rapamycin; Ley, S. V. et al. Angew. Chem. Int. Ed. 2007, 46, 591 –597. (pdf) (pdf of presentation).

1/29: M. Sprachman: Synthesis of (rac)-epi-Stegobinone Utilizing Silacyclopropanes as Synthetic Intermediates," Calad, S.A.; Cirakovic, J.; Woerpel, K.A. J. Org. Chem. 2007, 72, 1027-1030. (pdf) (pdf of presentation).

2/19: S. Osman: "Total Synthesis of (+)-Nakadomarin A" Ian S. Young and Michael A. Kerr, J. Am. Chem. Soc. 2007, 129, 1465-14699. (pdf) (pdf of presentation).

2/26: A. Rosenberg: "Synthesis of (-)trans-Tetrahydrocannabinol via Mo-Catalyzed Asymmetric Allylic Alkylation Reaction" Trost, B.M.; Dogra, K.; Org Lett ASAP. (pdf) (pdf of presentation).

2/26: A.-H. Yeh: Synthesis of a Ring-Expanded Bryostatin Analogue; Barry M. Trost,* Hanbiao Yang, Oliver R. Thiel, Alison J. Frontier, and Cheyenne S. Brindle; J. Am. Chem. Soc. 2007; ASAP Article; DOI: 10.1021/ja067305j. (pdf) (pdf of presentation).

3/12: F. Petronijevic: Total Synthesis of Marinomycins A-C and of Their Monomeric Counterparts Monomarinomycin A and iso-Monomarinomycin A; K. C. Nicolaou,* Andrea L. Nold, Robert R. Milburn, Corinna S. Schindler, Kevin P. Cole, and Junichiro Yamaguchi; J. Am. Chem. Soc. 2007, 129, 1760-1768. (pdf) (pdf of presentation).

3/19: P. Wipf: Taillier, C.; Gille, B.; Bellosta, V.; Cossy, J., "Synthetic Approaches and Total Synthesis of Natural Zoapatanol." J. Org. Chem. 2005, 70, 2097-2108.

3/26: Discussion of Exam II.

4/2: B. Hutnick: Li, C.; Chan, C.; Heimann, A. C.; Danishefsky, S. J., "Total synthesis of phalarine." Angew. Chem., Int. Ed. 2007, 46, 1448-1450.Li, C.; Chan, C.; Heimann, A. C.; Danishefsky, S. J., "On the rearrangement of an azadpiroindolenine to a precursor to phalarine: mechanistic insights." Angew. Chem., Int. Ed. 2007, 46, 1444-1447. (pdf) (pdf of presentation).

4/2: A. Rosenberg: "Novel Photolabile Protecting Group for Carbonyl Compounds" Wang, P.; Hu, H.; Wang, Y.; Org Lett ASAP. (pdf) (pdf of presentation).

4/9: S. Osman: "Total synthesis of marine natural products without using protecting groups" Baran, P. S.; Maimone, T. J.; Richter, J. M., Nature (London, United Kingdom) 2007, 446, 404-408. (pdf) (pdf of presentation).

4/9: M. Manojlovic: "Total synthesis of Papulacandin D." Denmark, S. E.; Regens, C. S.; Kobayashi, T. J. Am. Chem. Soc. 2007, 129, 2774-2776. (pdf) (pdf of presentation).

4/16: J. Hale: " Evans, D. A.; Nagorny, P.; Reynolds, D. J.; McRae, K. J., "Enantioselective synthesis of oasomycin A, part II: synthesis of the C29-C46 subunit." Angew. Chem., Int. Ed. 2007, 46, 541-544." (pdf) (pdf of presentation).

4/16: S. Spagna: "Sanchez-Izquierdo, F.; Blanco, P.; Busque, F.; Alibes, R.; de March, P.; Figueredo, M.; Font, J.; Parella, T. Org. Lett.; (Letter); 2007; ASAP." (pdf) (pdf of presentation).

4/16: M. Osipov: "Konrad Tiefenbacher, Vladimir B. Arion, and Johann Mulzer "A Diels–Alder Approach to (-)-Ovalicin" Angew. Chem. Int. Ed. 2007, 46, 2690 –2693" (pdf) (pdf of presentation).