876954-01-7Relevant academic research and scientific papers
An efficient synthesis of the tamandarin B macrocycle
Lassen, Kenneth M.,Lee, Jisun,Joullié, Madeleine M.
supporting information; body text, p. 1635 - 1638 (2010/06/14)
A reliable, high yielding cyclization protocol for the macrocycle of tamandarin B is presented. This strategy will facilitate the synthesis of side chain analogs.
Total synthesis and biological evaluation of tamandarin B analogues
Adrio, Javier,Cuevas, Carmen,Manzanares, Ignacio,Joullie, Madeleine M.
, p. 5129 - 5138 (2008/02/07)
(Chemical Equation Presented) Tamandarins A and B are a class of marine natural cyclodepsipeptides with structures and biological activities closely related to those of the didemnins. The easier synthetic access to tamandarins accelerates the preparation of new macrocyclic derivatives of this family of antitumor, antiviral, and immunosuppressive compounds. The optimization of the previously reported synthetic route to tamandarins by changing the macrolactamization site from Nst1 and Thr6 to Pro 4 and N,O-Me2Tyr5 residues led to a significant improvement in the reaction yield. Using this new synthetic approach, four new macrocyclic analogues of tamandarin B were prepared and evaluated for anticancer activity. These results provide further insight into the structure-activity relationship of the tamandarins and didemnins.
Synthesis and biological evaluation of tamandarin B analogues
Adrio, Javier,Cuevas, Carmen,Manzanares, Ignacio,Joullie, Madeleine M.
, p. 511 - 514 (2007/10/03)
The synthesis of two tamandarin B analogues in which the N,O-Me 2Tyr5 unit was replaced by N-Me-phenylalanine (N-MePhe5) and (S)-2-(methylamino)-3-(naphthalen-2-yl)propanoic acid (N-MeNaphth5) is described. The
