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

Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy.

The first total syntheses of (+)-zampanolide (1) and (+)-dactylolide (2), members of a new class of tumor cell growth inhibitory macrolides, have been achieved. Key features of the unified synthetic scheme included the stereocontrolled construction of the cis-2,6-disubstituted tetrahydropyran via a modified Petasis-Ferrier rearrangement, a highly convergent assembly of the macrocyclic domain, and, in the case of zampanolide, a Curtius rearrangement/acylation tactic to install the N-acyl hemiaminal. The complete relative and absolute stereochemistries for both (+)-zampanolide and (+)-dactylolide were also assigned, albeit tentatively in the case of (+)-zampanolide (1).[1]

References

  1. Total syntheses of (+)-zampanolide and (+)-dactylolide exploiting a unified strategy. Smith, A.B., Safonov, I.G., Corbett, R.M. J. Am. Chem. Soc. (2002) [Pubmed]
 
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