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Part I. The Development of a Strategy for the Asymmetric Synthesis of PPAPs: Application to the Total Synthesis of (+)- and (–)-Clusianone
Part II. Progress Toward the Asymmetric Total Synthesis of Brasilicardin A
- Abstract:
The development of a strategy for the asymmetric synthesis of a large portion of the polycyclic polyprenylated acyl phloroglucinols via N-amino cyclic carbamate hydrazones, and its application to the first asymmetric total synthesis of both (+)- and (-)-clusianone is discussed. The clusianones are synthesized with an er of 99:1 and their anti-HIV activity is found to be 1.53 and 1.13 uM, respectively. A library of clusianone-like compounds is synthesized and their biological activity has been probed.
Next, efforts towards the total synthesis of brasilicardin A are reported. Brasilicardin A is a molecule of interest to synthetic chemists for its unusual anti/syn/anti-perhydrophenanthrene core, as well as to biologists for its interesting biological activity. It has been shown to possess both immunosuppressive activity and cytotoxicity against a variety of cell lines. An appropriate model system was synthesized, and conditions were established using a pinene-based aldol reaction to synthesize the B-methoxy-a-amino ester side chain of the molecule. Next, efforts toward the synthesis of the anti-syn-anti- perhydrophenanthrene core are discussed.
Ph.D. Dissertation Defense Examination Seminar
Departmental Seminar