Areas of Research Interest: Synthetic Methodology and Medicinal Chemistry
M. N. Rao, M. A. McGuigan, X. Zhang, W. A. Kinney*, M. Bulliard, B. Laboue, N. E. Lee* J. Org. Chem. 1997, 62, 4541; N. E. Lee, G. S. Reddy, A. J. Brown, P. G. Williard Biochemistry 1997, 36, 9429;
"Chiral Reduction of a Steroidal a,b -Alkynone side Chain", Annise P. Berger, Nancy E. Lee. 27th Northeast Regional Meeting of the American Chemical Society, Sarotoga Springs, NY. June 1997.]
"Chiral Reduction of Steroidal a,b-Alkynone Side Chains", T. B. Gooding, A. P. Berger, N. E. Lee 216th National Meeting of the American Chemical Society, Boston, MA. August, 1998.
"Chiral Reduction of a Steroidal a,b-Alkynone t-Butyl side Chain", Ayako Honda, T. B. Gooding, A. P. Berger, N. E. Lee. Northeast Student Chemistry Research Conference, M. I. T., Cambridge, MA. April 1999.
Our second project involves studies toward synthesis of cyclic allylic imidates and their [3,3] sigmatropic rearrangement in a novel ring expansion reaction to produce medium size lactams. As a prerequisite for investigating the [3,3] rearrangement, the synthesis of five and six-member cyclic imidates was required. We synthesized 5-hydroxypentanenitriles and 4-hydroxybutanenitriles to study the intramolecular cyclization process under basic conditions. 4-hydroxybutanenitriles were more facile and cyclized to afford the desired five-member cyclic imidates. Several five-member cyclic allylic imidates were synthesized and we are currently studying the proposed [3,3] rearrangement to a seven-member ring lactams.
"Base-catalyzed cyclization of a hydroxy pentanenitrile" Kieuchinh T. Tran, Nancy E. Lee. 35th Annual American Chemical Society Undergraduate Research Symposium, Boston University, Boston, MA. April 27, 1996.
"Study of Synthesis and Rearrangement of Cyclic Imidates" Kathryn Schreiber, Yilin Shao, Natalie Hill, Kiieuchinh Tran, Nancy Lee. 216th National Meeting of the American Chemical Society, Boston, MA. August, 1998.
(Note: Simmons undergraduate co-workers are underlined)