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Synthesis 1991; 1991(6): 435-438
DOI: 10.1055/s-1991-26485
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Stereoselective Synthesis of a Building Block Corresponding to the C(1)-to-C(7) Moiety of 14-Membered Macrolide Antibiotics

Marco Born* , Christoph Tamm
  • *Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
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Publication Date:
29 April 2002 (online)

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The synthesis of 2′,6′-dimethylphenyl (2R,3R,4R, 5R,6S)-3-hydroxy-5,7-isopropylidenedioxy-2,4,6-trimethylheptanoate (13) a synthon for the C(1)-to-C(7) segment of a number of 14-membered macrolide antibiotics is described, starting from the meso-diester 3. Introduction of the new chiral centres was achieved by a threo-aldol condensation with the lithium 1-hydroxy-2,6 dimethylphenyl-1-propenoate (12) leading to the hydroxy ester 13. The absolute configuration of the synthon was proven by comparing the spectroscopic data and the optical rotation with the enantiomer.

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