Chemistry, School of Molecular Sciences, University of Western Australia, Perth 6009, Australia.
Microbial Screening Technologies, Smithfield, NSW 2164, Australia.
J Nat Prod. 2020 Dec 24;83(12):3623-3634. doi: 10.1021/acs.jnatprod.0c00800. Epub 2020 Dec 14.
The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from ,-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.
2,6'-二氢血根碱天然产物二羟血根碱及其非天然 3,6'-异构体异二羟血根碱已分别从β-二乙基千里光碱酰胺经 7 步反应全合成，总产率分别为 12%和 13%。这些合成方法与拉蒙那酮（7-甲基胡桃醌）不同，包括关键的铃木-宫浦偶联反应。二羟血根碱、异二羟血根碱和几种合成前体对小鼠骨髓瘤 NS-1 细胞系具有强大而选择性的细胞毒性，而对新生儿包皮细胞无毒性。
