205386-57-8Relevant academic research and scientific papers
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and (±)-Isoflavipucine
Mizutani, Shoma,Komori, Kenta,Taniguchi, Tohru,Monde, Kenji,Kuramochi, Kouji,Tsubaki, Kazunori
, p. 9553 - 9556 (2016)
A biomimetic synthesis of naturally occurring lactams rubrobramide, flavipucine, and isoflavipucine is described. The key step is a regioselective Darzens reaction between isobutyl glyoxal and an α-bromo-β-ketoamide. The construction of the core tricyclic ring system of rubrobramide was achieved by a cascade reaction in a single step from an α,β-epoxy-γ-lactam. Furthermore, the absolute configuration of naturally occurring (+)-rubrobramide was determined by vibrational circular dichroism. (±)-Flavipucine and (±)-isoflavipucine were synthesized from an epoxyimide, which was prepared by reaction of isobutyl glyoxal with a protected α-bromo-β-ketoamide. Deprotection of the epoxyimide and formation of the pyridone ring gave (±)-flavipucine, which was converted into (±)-isoflavipucine by thermal isomerization.
Synthesis, antibacterial and cytotoxic evaluation of flavipucine and its derivatives
Kusakabe, Yasuha,Mizutani, Shoma,Kamo, Shogo,Yoshimoto, Tatsuki,Tomoshige, Shusuke,Kawasaki, Tsuneomi,Takasawa, Ryoko,Tsubaki, Kazunori,Kuramochi, Kouji
, p. 1390 - 1394 (2019)
The antibacterial and cytotoxic activity of seven racemic lactams and both enantiomers of flavipucine were evaluated. Of the compounds tested in this study, flavipucine and phenylflavipucine displayed bactericidal activity against Bacillus subtilis. These
Enantioselective total synthesis of (+)-rubrobramide, (+)-talaramide A, and (?)-berkeleyamide D by a skeletal diversification strategy
Tanaka, Kosaku,Kobayashi, Kenichi,Kogen, Hiroshi
supporting information, p. 9780 - 9783 (2021/09/30)
A unified synthesis of (+)-rubrobramide, (+)-talaramide A, and (?)-berkeleyamide D was achieved from the vinylogous esters by a skeletal diversification strategy based on regioselective 5-exoor 6-endocyclization. This report describes the first enantioselective total synthesis of (+)-rubrobramide and (+)-talaramide A. Additionally, synthetic spirocyclic lactam compounds, including (?)-berkeleyamide D, showed moderate inhibitory activity against amyloid-β aggregation for the potential treatment of Alzheimer's disease.
