Download PDF
Synthesis 1991; 1991(6): 435-438
DOI: 10.1055/s-1991-26485
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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.