SYNTHESIS OF NATURAL AND UNNATURAL PRODUCTS
Total Synthesis of Ingenol via the Intramolecular Dioxenone
Photocycloaddition
We have applied the intramolecular dioxenone photocycloaddition
reaction developed in our laboratory to the first synthesis of
the tricyclic core of ingenol 1 containing the inside-outside
stereochemical relationship. We have since extended this work
to the synthesis of the first high-affinity ligand for protein
kinase C. Work in our laboratory is directed towards combining
these two efforts in the completion of the synthesis of ingenol.
Total Synthesis of Eleutherobin via Tandem Diels-Alder Cycloaddition
We have recently developed the tandem Diels-Alder reaction as
a powerful method for the stereoselective construction of polycyclic
ring systems. We are currently applying this methodology to an
approach to the synthesis of eleutherobin, 4, a potent Taxol-like
agent.
New Synthetic Methodology Based on the Vinylogous Amide Photocycloaddition
We have developed the vinylogous amide photocycloaddition/fragmentation/Mannich
closure for the synthesis of perhydroindoles and have recently
applied this methodology to the first synthesis of manzamine A.
We have recently extended this protocol to the construction of
azobicyclo[3.2.1]octane systems and are applying this new sequence
to the synthesis of sarain A, 3.
Design and Synthesis of Novel Foldamers and Scaffolds from
b-Amino Acids We have recently designed novel b-amino acid
structures and have demonstrated that they can be transformationed
into dimers and tetramers, i.e., 4, which adopt well-defined helical
conformations. Further studies on theses systems to give novel
scaffold structures for peptidomimetic synthesis is currently
in progress in our laboratory
Selected Publications
Back to faculty page
|
