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Total Synthesis of (−)-Virginiamycin M2

Authors


  • Financial support was obtained from NIH CA 53604. The authors are grateful to Dr. Baptiste Ronan at Sanofi-Aventis for 1H NMR spectrum comparison of compound 22, Dr. Yun Zhang at Novartis Institute (Cambridge, MA), Dr. Jason T. Lowe at the Broad Institute (Cambridge, MA) for helpful discussions, Dr. Paul Ralifo and Dr. Norman Lee at Boston University for assistance with NMR and HRMS measurements.

Abstract

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Has a nice ring to it: A concise and modular total synthesis of the naturally occurring antibiotic virginiamycin M2 is described. A Barbier-type cyclization was used to close the 23-membered macrocycle and deliver virginiamycin M2 in 19 steps from a chiral organosilane.

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