Glenn A. Pullella, Daniel Vuong, Ernest Lacey, and Matthew J. Piggott
J. Nat. Prod., 2020, 83, 3623-3634.
Publication Date: December 14, 2020
https://doi.org/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.
