Coltart Research Group
(Back row: Don Coltart, Scott Sauer, John Hatcher, Brad Robertson
Front Row: Michelle Garnsey, Sarah Wengryniuk, Stacey Turner, Mark Kohler, John Knight)
Group News
12/09/11: Congratulations to Dr. John Hatcher on successfully defending his Ph.D. dissertation!! Among a number of other things, John has been engaged in the development of new approaches to the α-functionalization of ketones and aldehydes via umpolung additions. These studies have culminated in the first Cu(I) addition of Grignard reagents to in situ derived azoalkenes. John's method is remarkable in its ability to deliver highly sterically hindered compounds, including those possessing up to three contiguous quaternary centers, that would be extremely difficult or impossible to generate using conventional enolate-based methods. John has extended the fundamental aspects of this reactivity to the development of the first catalytic asymmetric method for asymmetric ketone α-sulfenylation. John will begin his postdoctoral studies in Professor Gray’s lab at the Harvard Medical School in January, 2012.
10/01/11: Congratulations to Brad and Sarah on recently completing the first asymmetric total synthesis of apratoxin D employing a variety of strategies, including our recently reported ACC methodology. This compound displays nanomolar cytotoxicity against H-460 lung cancer cells.
09/27/11: Congratulations to Scott on accepting a postdoctoral position in the Devi group at the Duke University Medical Center.
08/26/11: Congratulations to Michelle on accepting a postdoctoral position in the Overman group at UC Irvine.
08/01/11: Congratulations to Michelle, Sarah, Brad, and Stacey on receiving departmental fellowships. Michelle received the Paul M. Gross Fellowship, Sarah received the Kathleen Zielek fellowship, Brad received the C. R. Hauser fellowship and Stacey received the Burrows welcome fellowship.
05/11/11: John K. and Scott have just had their manuscript describing the asymmetric total synthesis of the anti-malarial drug (+)-mefloquine via our asymmetric ACC auxiliaries recently published in Org. Lett. Congratulations guys!
04/20/11: Congratulations to Sarah and Dan on having their manuscript entitled "Regioselective Asymmetric α,α-Bisalkylation of Ketones via Complex Induced Syn-Deprotonation of Chiral N-Amino Cyclic Carbamate Hydrazones" accepted for publication in J. Am. Chem. Soc.
04/20/11: Michelle Garnsey has recently completed the asymmetric total synthesis of both (+)- and (–)-clusianone using our newly developed asymmetric ACC alkylation method. These compounds and certain structural analogs were recently evaluated for their biological activity in collaboration with the Kwiek lab at the Ohio State University with unanticipated results. The full account of this work has been published in Bioorg. Med. Chem. Lett.
04/20/11: Congratulations to John K. and Scott on completing the asymmetric total synthesis of both the (+)- and (–)-enantiomers of the anti-malarial drug mefloquine. They did so using, as a key step, a new asymmetric Darzens reaction that John developed utilizing our ACC auxiliaries. An account of the synthesis has been submitted for publication.
04/15/11: Congratulations to Stacey Turner on completing her preliminary exam! Stacey has made impressive strides in the short time she has been with us working to understand the outcome and mechanistic details of our recently described ACC alkylation method. We have high hopes for her future research!
04/04/11: Congratulations to Dr. Scott Sauer on successfully defending his Ph.D. thesis. The primary focus of Scott’s research has been on developing novel approaches to the direct aldol addition and related reactions. Early on, he participated in the development of an anti-selective four-component direct aldol addition. More recently, Scott developed a reductive soft enolization approach to the syn-aldol that was published as a communication in J. Am. Chem. Soc. In addition to his methodology studies, Scott has been involved in the asymmetric total synthesis of the anti-malarial drug, Mefloquine. A manuscript describing this work has just been submitted for publication. Stay tuned.
12/13/10: Congratulations to Emily (Dr. Tarsis!) on successfully defending her Ph.D. thesis! During her time in our group Emily has made important contributions to several projects. Notable among these, she has developed a useful alternative to the widely known Morita-Baylis-Hillman reaction that not only significantly reduces the duration of the reaction (from days to hours), but also broadens its synthetic scope to the use of β-substituted α,β-unsaturated carbonyls and/or sterically hindered aldehydes. Most recently, Emily has made impressive strides towards the asymmetric total synthesis of apratoxin D, using an approach based on our new and developing ACC alkylation chemistry. Emily will begin her postdoctoral studies at Scripps Florida in the Micalizio group in February, 2011.
11/01/10: Congratulations to Dan and Sarah, whose manuscript describing a collaborative effort with the Houk laboratory to determine the origins of stereoselectivity in the alkylation of ACC hydrazones, has been published in the Journal of Organic Chemistry.
10/25/10: Congratulations to Michelle, Dan, and Julianne paper on their recent Org. Lett. publication describing the asymmetric total synthesis of (+)-clusianone.
09/30/10: Congratulations to Julianne, Rachel, Emily, and Insun on their latest publication entitled Direct Carbon–Carbon Bond Formation via Soft Enolization: Aldol Addition of α-Halogenated Thioesters that will appear in the forthcoming Emerging Investigators issue of Chemical Communications.
09/14/10: Congratulations to Scott and Michelle on having their manuscript entitled Direct Carbon–Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes accepted to the Journal of the American Chemical Society as a communication!
07/01/10: Congratulations to Mark, Julianne, and Michelle for their Organic Letters article entitled Direct Carbon–Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters.