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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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A convergent synthesis of the proposed structure of antitumor depsipeptide stereocalpin A.

The total synthesis of the proposed structure of anticancer agent stereocalpin A is described. The synthesis features a diastereoselective synthesis of a 5-hydroxy-2,4-dimethyl-3-oxooctanoic acid unit with asymmetric anti- and syn-aldol reactions as the key steps. Initial cycloamidation led to complete epimerization at the C-11 stereocenter due to unique steric constraints in the 12-membered depsipeptide ring. A late-stage methylation strategy led to the synthesis of the proposed structure of stereocalpin A.[1]

References

  1. A convergent synthesis of the proposed structure of antitumor depsipeptide stereocalpin A. Ghosh, A.K., Xu, C.X. Org. Lett. (2009) [Pubmed]
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