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DOI: 10.1055/s-0030-1258711
Synthesis of (-)-Virginiamycin M2
Contributor(s):Steven V. Ley, Philippa B. CranwellBoston University, USA
Total Synthesis of (-)-Virginiamycin M2
Angew. Chem. Int. Ed. 2010, 49: 6165-6168
Publication History
Publication Date:
21 October 2010 (online)
Key words
virginiamycin M2 - samarium(II) iodide mediated cyclization - chiral silanes
Significance
Virginiamycin M2 is a naturally occurring antibiotic produced by Streptomyces. Derivatives of the virginiamycins display potent antibiotic activity against methicillin-, erythromycin-, and vancomycin-resistant S. aureus and have led to drugs which have been used to treat severe Gram-positive bacterial infections.
Comment
The total synthesis of virginiamycin M2 has been achieved in ten steps. Use of enantiopure silane A installed the desired olefin geometry and stereochemical configuration in B with high selectivity. The formation of diene E was achieved using a titanium-mediated reductive coupling between C and D using the preprepared lithium alkoxide of D.