663919-01-5Relevant academic research and scientific papers
Total synthesis of spiruchostatin A via chemoselective macrocyclization using an accessible enantiomerically pure latent thioester
Calandra, Nicole A.,Cheng, Yim Ling,Kocak, Kimberly A.,Miller, Justin S.
supporting information; experimental part, p. 1971 - 1974 (2009/09/08)
HDAC inhibitor Spiruchostatin A was synthesized via a route that differs significantly from previously reported routes. The key step involves a latent thioester that initiates a chemoselective transformation similar to native chemical ligation to form 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
