182360-34-5Relevant academic research and scientific papers
The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry
Lan, Hong-Qiao,Ruan, Yuan-Ping,Huang, Pei-Qiang
supporting information; experimental part, p. 5319 - 5321 (2010/09/03)
Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3- methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.
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
Total Synthesis of Spiruchostatin A, a Potent Histone Deacetylase Inhibitor
Yurek-George, Alexander,Habens, Fay,Brimmell, Matthew,Packham, Graham,Ganesan
, p. 1030 - 1031 (2007/10/03)
The total synthesis of spiruchostatin A was accomplished, unambiguously confirming its structure. Key steps included the use of the Nagao thiazolidinethione auxiliary for a diastereoselective acetate aldol reaction and as an activated acylating agent for amide formation, and macrolactonization by the Yamaguchi protocol. Spiruchostatin A is shown to have biological activity similar to that of FK228, a potent histone deacetylase (HDAC) inhibitor in clinical trials. The spiruchostatin A analogue, epimeric at the β-hydroxy acid, is inactive, highlighting the importance of stereochemistry at this position for interactions with HDACs. Copyright
