Ph.D.: Yale University, 1988 Postdoctoral Fellow: NSF fellow at Harvard University, 1988-90 Awards: Alfred P. Sloan Foundation Fellow, 1996 American Cancer Society Junior Faculty Research Award, 1994 Camille and Henry Dreyfus New Faculty Award, 1990

Synthesis

Synthetic Methods and Total Synthesis The Sammakia group is interested in various aspects of organic synthesis and is currently engaged in projects directed at the discovery of new catalysts for asymmetric synthesis, mechanistic investigations of reactions which proceed with high levels of selectivity, and the total synthesis of biologically active natural products.

Gazaille, J. A.; Abramite, J. A.; Sammakia, T. "Toward the Synthesis of (+)-Peloruside A via an Intramolecular Vinylogous Aldol Reaction" Org. Lett. 2012, 14, 178.DOI: 10.1021/ol202966m Zhang, Y.; Arpin, C. C.; Cullen, A. J.; Mitton-Fry, M. J.; Sammakia, T. "Total Synthesis of Dermostatin A" J. Org. Chem. 2011, 76,7641. DOI: 10.1021/jo2012658 Hao, X.; Nguyen, T.; Daniel B. Kearns, D. B.; Arpin, C. C.; Ray Fall, R.; Sammakia, T. "New inhibitors of colony spreading in Bacillus subtilis and Bacillus anthracis" Bioorg. Med. Chem. Lett. 2011, 21, 5583. DOI: 10.1016/j.bmcl.2011.06.082 Crane, Z. D.; Nichols, P. J.; Sammakia, T.; Stengel, P. J. "Synthesis of Methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann Rearrangement Utilizing Trichloroisocyanuric Acid as an Oxidant" J. Org. Chem., 2011, 76, 277–280. DOI:10.1021/jo101504e Mai, C.-K.; Sammons, M. F.; Sammakia, T. "α-Arylation of 3-Aryloxindoles" Org. Lett. 2010, 12, 2306. DOI: 10.1021/ol100666v Mai, C.-K.; Sammons, M. F.; Sammakia, T. "A Concise Formal Synthesis of Diazonamide A by the Stereoselective Construciton of the C10 Quaternary Center" Angew. Chem., Int. Ed. 2010, 49, 2397. DOI: 10.1002/anie.200906318 (Highlighted by: Synfacts, 2010, 6, 622. Most Accessed Arcticle in March, 2010.) Abramite, J. A.; Sammakia, T. "Application of the Intramolecular Vinylogous Yamamoto Aldol Reaction to the Synthesis of Macrolides " Org. Lett. 2007, 9, 2103. DOI: 10.1021/ ol0704901 Mitton-Fry, M. J.; Cullen, A. J.; Sammakia, T. "The Total Synthesis of the Oxopolyene Macrolide RK-397" Angew. Chem., Int. Ed. 2007, 46, 1066. DOI: 10.1002/anie.200602601 Seiwert, S. D.; Blatt, L. M.; Andrews, S. W.; Martin, P.; Schumacher, A.; Barnett, B. R.; Eary, T. C.; Kaus, R.; Kercher, T.; Liu, W.; Lyon, M.; Nichols, P.; Wang, B.; Sammakia, T.; Kennedy, A.; Jiang, Y. "Novel Macrocyclic Inhibitors of Hepatitis C Virus Replication" International Patent WO 2007/015824 A2 Sammakia, T.; Abramite, J. A.; Sammons, M. F. "Enamines" In Science of Synthesis, Trost, B. M., Molander, G. A., Eds.; Theime: Stuttgart, Germany, 2006; Vol. 33, pp 405-442. Zhang, Y.; Sammakia, T. "Double Diastereoselective Acetate Aldol Reactions with Chiral N-Acetyl Thiazolidinethione Reagents" J. Org. Chem. 2006, 71, 6262. DOI: 10.1021/jo0605694 Notte, G. T.; Sammakia, T. "Kinetic Resolution of Protected a-Amino Acid Derivatives by a Chiral O-Nucleophilic Acyl Transfer Catalyst" J. Am. Chem. Soc. 2006, 128, 4230. DOI: 10.1021/ja058010t Notte, G. T.; Sammakia, T. "Kinetic Resolution of a-Acetoxy N-Acyl Oxazolidinethiones by a Chiral O-Nucleophilic Acyl Transfer Catalyst" J. Am. Chem. Soc. 2005, 127,13502. DOI: 10.1021/ja053743z Sammakia, T.; Johns, D. M.; Kim, G.; Berliner, M. A. "Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin" J. Am. Chem. Soc. 2005, 127, 6504. DOI: 10.1021/ja043506g Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. "Remote Functionalization of Pyridine Rings via the Halogen Dance Reaction: Application to the Total Synthesis of Caerulomycin and WS75624 B" In "Strategies and Tactics in Organic Synthesis" Academic Press: New York, 2005; Vol 6, pp 415-436. Zhang, Y.; Sammakia, T. "Synthesis of a New N-Acetyl Thiazolidinethione Reagent and Its Application to a Highly Selective Asymmetric Acetate Aldol Reaction" Org Lett. 2004, 6, 3139. DOI: 10.1021/ol048810t Cullen, A. J.; Sammakia, T. "Highly Selective Reduction of Acyclic b-Alkoxy Ketones to Protected syn-1,3-Diols" Org. Lett. 2004, 6, 3143. DOI: 10.1021/ol048801k Zhang, Y.; Phillips, A. J.; Sammakia, T. "Highly Selective Asymmetric Acetate Aldol Reactions of an N-Acetyl Thiazolidinethione Reagent" Org. Lett. 2004, 6, 23. DOI: 10.1021/ol036020y Stangeland, E. L.; Sammakia, T. "Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B" J. Org. Chem. 2004, 69, 2381. DOI: 10.1021/jo0351217 Wayman, K. A.; Sammakia, T. "O-Nucleophilic Amino-Alcohol Acyl-Transfer Catalysts: the Effect of Acidity of the Hydroxyl Group on the Activity of the Catalyst" Org. Lett. 2003, 5, 4105. DOI: 10.1021/ol035510n Sammakia, T.; Stangeland, E. L.; Whitcomb, M. C. "Total Synthesis of Caerulomycin C via the Halogen Dance Reaction" Org. Lett. 2002, 4, 2385. DOI: 10.1021/ol026135m. Sammakia, T.; Hurley, T. B. "Enhanced Selectivities for the Hydroxyl-Directed Methanolysis of Esters Using the 2-Acyl-4-Aminopyridine Class of Acyl Transfer Catalysts: Ketones as Binding Sites" J. Org. Chem. 2000, 65, 974. DOI: 10.1021/jo991202k Sammakia, T.; Hurley, T. B. "Studies of the Mechanism of Action of 2-Formyl-4-pyrrolidinopyridine (FPP): Evidence for General Base Catalysis" J. Org. Chem. 1999, 64, 4652. DOI: 10.1021/jo982281n Sammakia, T.; Jacobs, J. S. "Picolinic Acid as a Partner in the Mitsunobu Reaction and Subsequent Hydrolysis of Picolinate Esters Under Essentially Neutral Conditions with Copper Acetate in Methanol" Tetrahedron Lett. 1999, 40, 2685. DOI: 10.1016/S0040-4039(99)00332-9 Stangeland, E. L.; Sammakia, T. "New Chiral Ligands for the Asymmetric Copper Catalyzed Conjugate Additions of Grignard Reagents to Enones" Tetrahedron 1997, 53, 16503. DOI: 10.1016/S0040-4020(97)01031-4 Sammakia, T.; Stangeland, E. L. "Asymmetric Transfer Hydrogenation with Ruthenium Complexes of Chiral Ferrocenyl Oxazolines" J. Org. Chem. 1997, 62, 6104. DOI: 10.1021/jo9711044 Sammond, D. M.; Sammakia, T. "A Mild Synthesis of Furans from g-Hydroxy-a,b-Unsaturated Ketones" Tetrahedron Lett. 1996, 37, 6065. DOI: 10.1016/0040-4039(96)01316-0 Sammakia, T.; Hurley, T. B. "2-Formyl-4-pyrrolidinopyridine (FPP): A New Catalyst for the Hydroxyl-Directed Methanolysis of Esters" J. Am. Chem. Soc. 1996, 118, 8967. DOI: 10.1021/ja9613623 Sammakia, T.; Hurley, T. B.; Sammond, D. M.; Smith, R. S.; Sobolov, S. B.; Oschger, T. R. "Dihydroxylation and Oxidative Cleavage of Olefins in the Presence of Sulfur" Tetrahedron Lett. 1996, 26, 4427. DOI: 10.1016/0040-4039(96)00879-9 Sammakia, T.; Latham, H. A. "On the Mechanism of Oxazoline-Directed Metallations: Evidence for Nitrogen-Directed Metallation" J. Org. Chem. 1996, 61, 1629. DOI: 10.1021/ jo951556l Sammakia, T.; Berliner, M. A. "Asymmetric Diels-Alder Reactions via Cyclic Vinyl-Oxocarbenium Ions" J. Org. Chem. 1995, 60, 6652. DOI: 10.1021/jo00102a006 Sammakia, T; Latham, H. A. "On the Use of Ferrocenyl Cations as Chiral Lewis Acids: Evidence for Protic Acid Catalysis" Tetrahedron Lett. 1995, 36, 6867. DOI: 10.1016/0040-4039(95)01440-S Sammakia, T.; Latham, H. A. "Ligand Effects on the Stereochemistry of the Metalation of Chiral Ferrocenyloxazolines" J. Org. Chem. 1995, 60, 6002. DOI: 10.1021/jo00124a003. Sammakia, T.; Latham, H. A.; Schaad, D. R. "Highly Diastereoselective Ortho Lithiations of Chiral Oxazoline Substituted Ferrocenes" J. Org. Chem. 1995, 60, 10. DOI: 10.1021/jo00106a005