Synthesis of New 14-Membered Macrolide Antibiotics via a Novel Ring Contraction Metathesis

A novel ring opening ring closing metathesis (ROM-RCM) was demonstrated for cyclic conjugated dienes, effecting the excision of a C2H2 unit and a net ring contraction. Applying the ring contraction metathesis, new 14-membered ring macrolide antibiotics were synthesized in a single step from existing...

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Bibliographic Details
Published in:Organic letters 2003-02, Vol.5 (4), p.443-445
Main Authors: Lazarova, Tsvetelina I, Binet, Sophie M, Vo, Nha H, Chen, Jason S, Phan, Ly T, Or, Yat Sun
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Drug Resistance
Erythromycin - chemistry
Josamycin - chemistry
Streptococcus pneumoniae - drug effects
Streptococcus pyogenes - drug effects
Structure-Activity Relationship
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Summary:A novel ring opening ring closing metathesis (ROM-RCM) was demonstrated for cyclic conjugated dienes, effecting the excision of a C2H2 unit and a net ring contraction. Applying the ring contraction metathesis, new 14-membered ring macrolide antibiotics were synthesized in a single step from existing 16-membered ring macrolides. This new class of macrolide antibiotics will provide access to new therapeutics for the treatment of macrolide-resistant bacterial infections.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027322n