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DOI: 10.1055/s-0030-1259286
Synthetic Studies towards Leiodermatolide: Rapid Stereoselective Syntheses of Key Fragments
Publikationsverlauf
Publikationsdatum:
23. Dezember 2010 (online)

Abstract
The synthesis of three key fragments of the novel 16-membered macrolide leiodermatolide is described. The stereotetrad-containing building block was prepared via a Marshall-Tamaru reaction on an aldehyde obtained by organocatalysis. For a second building block, a Marshall-Tamaru reaction was used as well. The side-chain fragment containing a hydroxy δ-lactone could be obtained by intramolecular Reformatsky reaction.
Key words
leiodermatolide - macrolide - Marshall-Tamaru reaction - intramolecular Reformatsky reaction - Fráter-Seebach alkylation
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- Supporting Information
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References and Notes
The following IC50 values are reported: A549, P399 = 3.3 nM, PANC-1 = 5.0 nM, DLD-1 = 8.3 nM, NCI-ADR-Res = 233 nM.