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Synlett 2011(2): 191-194
DOI: 10.1055/s-0030-1259286
DOI: 10.1055/s-0030-1259286
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthetic Studies towards Leiodermatolide: Rapid Stereoselective Syntheses of Key Fragments
Further Information
Publication History
Received
3 November 2010
Publication Date:
23 December 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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