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An RCM‐Based Total Synthesis of the Antibiotic Disciformycin B

Waser, Philipp ; Altmann, Karl‐Heinz

Angewandte Chemie (International ed.), 2020-09-28, Vol.59 (40), p.17393-17397 [Peer Reviewed Journal]

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  • Title:
    An RCM‐Based Total Synthesis of the Antibiotic Disciformycin B
  • Author: Waser, Philipp ; Altmann, Karl‐Heinz
  • Subjects: natural products ; disciformycin ; total synthesis ; macrocycles ; ring-closing metathesis ; Index Medicus
  • Is Part Of: Angewandte Chemie (International ed.), 2020-09-28, Vol.59 (40), p.17393-17397
  • Description: The total synthesis of the potent new antibiotic disciformycin B (2) is described, which shows significant activity against methicillin‐ and vancomycin‐resistant Staphylococcus aureus (MRSA/VRSA) strains. The synthetic route is based on macrocyclization of a tetraene substrate to the 12‐membered macrolactone core by ring‐closing olefin metathesis (RCM). Although macrocyclization was accompanied by concomitant cyclopentene formation by an alternative RCM pathway, conditions were established to give the macrocycle as the major product. Key steps in the construction of the RCM substrate include a highly efficient Evans syn‐aldol reaction, the asymmetric Brown allylation of angelic aldehyde, and the stereoselective Zn(BH4)2‐mediated 1,2‐reduction of an enone. The synthesis was completed by late‐stage dehydrative glycosylation to introduce the d‐arabinofuranosyl moiety and final chemoselective allylic alcohol oxidation. Large or small (ring), that was the question. The antibiotic disciformycin B has been synthesized in 18 linear steps from simple starting materials. The key step was the macrocyclization of the tetraene 7 by ring‐closing olefin metathesis (RCM).
  • Publisher: Germany
  • Language: English
  • Identifier: ISSN: 1433-7851
    EISSN: 1521-3773
    DOI: 10.1002/anie.202004589
    PMID: 32558021
  • Source: © ProQuest LLC All rights reserved
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