Synthetic Routes to a Constrained Ring Analog of Didemnin B.
The didemnin class of biologically active cyclodepsipeptides, isolated from a marine tunicate, has shown antitumor, antiviral, and immunosuppressive activities. Synthetic studies were undertaken to prepare a modified analog of one of the most potent congeners, didemnin B (1). The side chain of the isostatine unit was tethered into the macrocycle viaa cyclohexane ring in order to provide a more rigid conformation and determine the importance of this unit in bioactive compounds. This modification created a new macrocycle core and generated a diastereomeric mixture of a constrained analog of didemnin B (2).
Mayer
Scott C.
SC
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323.
Pfizenmayer
Amy J.
AJ
Joullié
Madeleine M.
MM