Total Synthesis of (+)‐Pleuromutilin

2013/04/15 by Neal J. Fazakerley, Matthew Helm, David J. Procter · 4 citations
Veterinary · Pharmacology, Toxicology and Pharmaceutics · Chemistry · #Veterinary medicine and infectious diseases #Pharmacological Effects of Natural Compounds #Quinazolinone synthesis and applications

paper · doi:10.1002/chem.201300968

openalex publication_date 2013/04/15 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/25

Abstract

The first enantiospecific total synthesis of the antibacterial natural product (+)-pleuromutilin has been achieved. The approach includes the synthesis of a non-racemic cyclisation substrate from (+)-trans-dihydrocarvone, a highly selective SmI2-mediated cyclisation cascade, an electron transfer reduction of a hindered ester, and the first efficient conversion of (+)-mutilin to the target.

Citations

• Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis
• Synthetic studies directed toward naturally occurring cyclooctanoids. 2. A stereocontrolled assembly of (.+-.)-pleuromutilin via a remarkable sterically demanding oxy-Cope rearrangement

Cited by

• Identification and manipulation of the pleuromutilin gene cluster from Clitopilus passeckerianus for increased rapid antibiotic production
• A modular and enantioselective synthesis of the pleuromutilin antibiotics
• Design and synthesis of molecular scaffolds with anti-infective activity
• Pleuromutilin [wikipedia]

Related

• A modular and enantioselective synthesis of the pleuromutilin antibiotics
• Expanding the pleuromutilin class of antibiotics by de novo chemical synthesis
• Heterologous expression reveals the biosynthesis of the antibiotic pleuromutilin and generates bioactive semi-synthetic derivatives
• A Click Chemistry Approach to Pleuromutilin Conjugates with Nucleosides or Acyclic Nucleoside Derivatives and Their Binding to the Bacterial Ribosome
• Identification and manipulation of the pleuromutilin gene cluster from Clitopilus passeckerianus for increased rapid antibiotic production