TY - JOUR
T1 - Total Synthesis of the Antitumor-Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
AU - Pullella, Glenn A.
AU - Vuong, Daniel
AU - Lacey, Ernest
AU - Piggott, Matthew J.
PY - 2020/12/24
Y1 - 2020/12/24
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85098796138&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.0c00800
DO - 10.1021/acs.jnatprod.0c00800
M3 - Article
C2 - 33314932
AN - SCOPUS:85098796138
VL - 83
SP - 3623
EP - 3634
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 12
ER -