159581-79-0Relevant 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 (2007/10/03)
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).
Synthetic studies of a constrained ring didemnin analog
Mayer,Pfizenmayer,Cordova,Li,Joullie
, p. 519 - 522 (2007/10/02)
An asymmetric Diels-Alder reaction in the presence of 3.0 M lithium perchlorate-diethyl ether was used to generate the initial stereochemistry for a cyclohexane amino acid (3), a key intermediate in the preparation of a fused ring didemnin analog. This constrained ring macrocycle should provide insight into the binding site conformation of the bioactive species.
Incorporation of an amino function in a (1S,2S,3R)-3-hydroxy-2-methoxy-1- cyclohexane carboxylic acid
Mayer,Joullie
, p. 2351 - 2365 (2007/10/02)
(1S,2S,3R)-3-Hydroxy-2-methoxy-1-cyclohexanecarboxylic acid was synthesized for the construction of an amino acid to be used in a constrained ring didemnin B analog (2). The amine functionality was introduced into the cyclohexane ring by reductive amination using sodium triacetoxyborohydride or by oxime formation followed by reduction.
