Total Synthesis of Psymberin

Psymberin was isolated in 2003 by our colleague Professor Phil Crews from the sponge Psammocinia.  The total synthesis of psymberin, as well as a library of analogs, is currently being pursued.

Total Synthesis of the Aciculitins

Aciculitins (A-C) were isolated by Professor John Faulkner and coworkers in 1996 from the lithistid sponge Aciculites orientalis. They are the first glycopeptidolipids isolated from a marine source. They are cytotoxic to the human-colon tumor cell line HCT-116 with an IC₅₀ value of 0.5 μg/mL. This total synthesis will clarify the absolute stereochemistry at the indicated carbons.

Total Synthesis of Cyclocinamide A

Cyclocinamide A was isolated in 1997 by our colleague Professor Phil Crews from the sponge Psammocinia. The total synthesis of 4(S),7(S),11(S),14(S)-cyclocinamide A, as well as a library of stereoisomers, is currently being pursued.

Modeling the Active Site of Cytochrome c oxidase

Ongoing work in our laboratory involves the use of lead arylation methodology in the synthesis of the active site pentapeptide found in the redox enzyme Cytochrome c oxidase. As can be seen from the diagram, this system contains an unusual tyrosine-histidine cross link that creates the cyclic system. Our studies in this area are in collaboration with our colleague Professor Ólöf Einarsdóttir.

Development of Novel β-Lactam Methodology

Our laboratory recently discovered a novel, direct route from amino acid derivatives to β-lactams, with full retention of stereochemistry and induction of a second chiral center.  We are currently exploring the scope and generality of this transformation, as well as its applicability to the synthesis of carbapenem derivatives.