2. Academic Validation
  3. Total Synthesis of the Antitumor-Antitubercular 2,6'-Bijuglone Natural Product Diospyrin and Its 3,6'-Isomer

Total Synthesis of the Antitumor-Antitubercular 2,6'-Bijuglone Natural Product Diospyrin and Its 3,6'-Isomer

  • J Nat Prod. 2020 Dec 24;83(12):3623-3634. doi: 10.1021/acs.jnatprod.0c00800.
Glenn A Pullella 1,  Daniel Vuong 2,  Ernest Lacey 2,  Matthew J Piggott 1
Affiliations

Affiliations

  • 1 Chemistry, School of Molecular Sciences, University of Western Australia, Perth 6009, Australia.
  • 2 Microbial Screening Technologies, Smithfield, NSW 2164, Australia.
PMID: 33314932 DOI: 10.1021/acs.jnatprod.0c00800
Abstract

The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.

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