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

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Asymmetric synthesis of the fully functional macrolide core of salicylihalamide: remote control of olefin geometry during RCM.

A catalysis-based approach to the core region 24 of the antitumor agents salicylihalamides A and B is reported. Key steps are two asymmetric hydrogenations of beta-keto esters 13 and 16 catalyzed by [(R)-BINAP.RuCl(2)](2).NEt(3) and an RCM-based macrocyclization effected by the NHC-containing ruthenium carbene 21. The stereochemical outcome of the latter reaction is controlled by remote substituents on the phenolic OH group of the cyclization precursor 23.[1]

References

  1. Asymmetric synthesis of the fully functional macrolide core of salicylihalamide: remote control of olefin geometry during RCM. Fürstner, A., Thiel, O.R., Blanda, G. Org. Lett. (2000) [Pubmed]
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