Jamison Research Group

The Jamison research group is in the Department of Chemistry at MIT. Research focuses on the development of cascade reactions, as well as multi-component coupling reactions directed toward the efficient syntheses of a variety of complex natural products.

The theme of the group's research is the discovery and application of new reactions for organic synthesis, and in a broader sense, selectivity is our fundamental interest. Many of the transformations we target are based on common structural motifs or functional group patterns present in molecules provided to us by Nature, while others have their origins in unexpected products we have obtained in the course of other experiments.

Several of the reactions under investigation can be classified as "multi-component coupling" or "cascade" processes, in which catalysts of various types promote the assembly of three (or more) molecules (intermolecular) or functional groups (intramolecular) in a selective fashion. Another aim of these projects is that the starting materials and reagents be easily prepared (or purchased) and that the products be useful "building blocks" or important carbocyclic or heterocyclic ring systems. Examples of these methods include enantioselective synthesis of allylic alcohols and allylic amines from alkynes, aldehydes (or imines, respectively), and organoboron reagents, catalyzed by Ni(0)-phosphine complexes, as well as catalytic three-component assembly of tetrahydrofurans.

In order to test the utility of these methods in specific contexts, we are employing them in the synthesis of several natural products that had originally suggested their development. In addition to terpestacin, acutiphycin, absinthin, waihoensene, and several amphidinolides, significant effort in the group is also directed toward the efficient synthesis of "ladder" polyether natural products, such as yessotoxin.