159517-29-0Relevant academic research and scientific papers
Synthetic routes to a constrained ring analog of didemnin B
Mayer, Scott C.,Pfizenmayer, Amy J.,Joullie, Madeleine M.
, p. 1655 - 1664 (1996)
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 via a 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).
Total synthesis of a conformationally constrained didemnin B analog
Xiao,Vera,Liang,Joullie
, p. 2734 - 2742 (2007/10/03)
The total synthesis of a didemnin B analogue containing a conformationally constrained replacement for the isostatine moiety is reported. Synthetic highlights include an improved preparation of 2-hydroxy-3-cyclohexenecarboxylic acid and a new strategy for accessing the macrocycle.
Stereoselective synthesis of a conformationally restricted β-hydroxy-γ-amino acid
Xiao, Dong,Carroll, Patrick J.,Mayer, Scott C.,Pfizenmayer, Amy J.,Joullie, Madeleine M.
, p. 3043 - 3046 (2007/10/03)
β-Hydroxy-γ-amino acids are a class of non-proteinogenic amino acids present in many important biologically active natural products. In conjunction with our research on didemnins, we designed and synthesized a sterically constrained β-hydroxy-γ-amino acid
