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
  • 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.