2. Academic Validation
  3. Total Synthesis and Determination of the Absolute Configuration of Parimycin

Total Synthesis and Determination of the Absolute Configuration of Parimycin

  • Org Lett. 2019 Sep 20;21(18):7665-7668. doi: 10.1021/acs.orglett.9b02999.
Day-Shin Hsu 1,  Jiun-Yi Huang 1
Affiliations

Affiliation

  • 1 Department of Chemistry and Biochemistry , National Chung Cheng University , Minhsiung 62102 , Taiwan.
PMID: 31512884 DOI: 10.1021/acs.orglett.9b02999
Abstract

The first total syntheses of (±)-parimycin and (R)-parimycin were accomplished from O-methylnaphthazarin (6) in nine synthetic steps. Intermolecular Diels-Alder reaction of 6 with diene 7, cyclodehydrogenation catalyzed by iodine-dimethyl sulfoxide, and sodium dithionite reduction were the key steps. The absolute configuration of natural parimycin was determined to be S.

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