Journal Club

CHEMISTRY 2320 – ADVANCED ORGANIC CHEMISTRY 2

Journal Club - Monday 5-5:50 PM in Eberly 228

Guidelines for Journal Club presentations:
 • Select a current (2008) 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 Org. Lett., J. Am. Chem. Soc., Angew. Chem. Int. Ed., or Methods in Organic Synthesis (MOS).

4/21/08 Recitation: • Peter Wipf: Special Topics & Practice for Final Exam.

4/14/08 Presentations: • Chris Rosenker: Total Synthesis of (-)-Pestalotiopsin A [Tadano et al., Angew. Chem. Int. Ed. 2008, early view; view] • Binbin Guo: New Chemistry with Old Functional Groups: On the Reaction of Isonitriles with Carboxylic Acids--A Route to Various Amide Types [Danishefsky et al., JACS 2008, ASAP; view].

4/7/08 Presentations: • Amir Faraji: A Predictably Selective Aliphatic C–H Oxidation Reaction for Complex Molecule Synthesis [Chen, M. S.; White, C. Science 2007, 318, 783; view] • Tingting Mo: Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway [Gevorgyan, V. et al., JACS 2008, ASAP; view]

3/31/08 Presentations: • Jared Hammill: Epoxy-Annulations by Reactions of alpha-Amido Ketones with Vinyl Sulfonium Salts. Reagent versus Substrate Control and Kinetic Resolution [Unthank, M. G.; Tavassoli, B.; Aggarwal, V. K., Org. Lett. 2008, ASAP; view] • Peter Wipf: Total Synthesis of (+)-Exiguolide [Lee, E. et al. Angew. Chem. 2008, 47, 1733].

3/24/08 Presentation: • Josh Osbourn: Michael Addition-Elimination Reactions of Chiral Enolates with Ethyl 3-Halopropenoates [Villarasa et al., Org. Lett. 2008, 10, 65-68]; view]

3/17/08 Presentation: • Peter Wipf: Chiral Version of the Burgess Reagent and Its Reactions with Oxiranes: Application to the Formal Enantiodivergent Synthesis of Balanol [Hudlicky, T. et al. J. Nat. Prod. XXXX, xxx, 000.

3/3/08 Presentation: • Peter Wipf: Stereoselective Total Synthesis of (−)-Perrottetinene and Assignment of Its Absolute Configuration [Kim, S. et al. Org. Lett. 2008, 10(2), 269-271.

2/25/08 Presentation: • Peter Wipf: A. Discussion of previous lecture problems. B. Cross Metathesis Strategies in Natural Product Total Synthesis.

2/18/08 Presentations: • Amir Faraji: Synthesis of Anthropomorphic Molecules: The NanoPutians [Tour et al., J. Org. Chem. 2003, 68, 8750; view] • Nora Jameson: Direct, Iridium-Catalyzed Enantioselective and Regioselective Allylic Etherification with Aliphatic Alcohols [Ueno et al., Angew. Chem. Int. Ed. 2008, Early View; view].

2/11/08 Presentations: • Jared Hammill: 3-Trifluoromethanesulfonamido-pyrrolidine: A General Organocatalyst for anti-Selective Mannich Reactions [Blanchet et al., Org. Lett. 2008, ASAP; view] • Andrey Solovyev: A Synthesis of RGD Model Cyclic Peptide by Palladium-Catalyzed Carbonylative Macrolactamization [Takahashi et al., Org. Lett. 2008, ASAP; view].

2/4/08 Presentation: • Eric Buck: Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation [Stoltz et al., J. Am. Chem. Soc. 2008, ASAP; view].

1/28/08 Presentations: • Chris Rosenker: A Chiral Pool Based Synthesis of Platensimycin [Nicolaou et al., Angew. Chem. Int. Ed. 2008, 47, 944; view] • Michael Cook: Ketone super silyl enol ethers in sequential reactions: Diastereoselective generation of tertiary carbinols in one pot [Boxer, M. B.; Akakura, M.; Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 1580-1582; view].

1/14/08 Presentations: • Nate Ware: Sequential Copper-Catalyzed Vinylation/Cyclization: En Efficient Synthesis of Functionalized Oxazoles [Buchwald et al., Org. Lett. 2007, 9, 5521; view] • Peter Wipf: Highly Efficient Asymmetric Synthesis of Fluvirucine A1 via Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA)-Lipase-Catalyzed Acetylation Tandem Process [Negishi & Liang, Org. Lett. 2008, ASAP; view]

Sample Presentation: Total Synthesis & Structure Elucidation of Bistramide [view]