Total Synthesis of (±)-Cylindrospermopsin was written by Xie, Chaoyu;Runnegar, Maria T. C.;Snider, Barry B.. And the article was included in Journal of the American Chemical Society in 2000.Recommanded Product: 59864-30-1 This article mentions the following:
The first total synthesis of the novel hepatotoxin (±)-cylindrospermopsin (I) has been accomplished in 20 steps from 4-methoxy-3-methylpyridine (II) in 3.5% overall yield. The substituted piperidine A ring III was generated stereospecifically by a four-step sequence using the addition of trimethylsilylethynylmagnesium bromide to II to give IV (Troc = CO2CH2CCl3) and stereospecific addition of vinylcuprate to IV to form V. The reaction of diamine VI (R1 = R2 = H; TBDMS = SiMe2CMe3) with cyanogen bromide produced the cyclic guanidine C ring of VI (R1R2 = C:NH). The key step in the synthesis was bromination of ketone VII (Cbz = CO2CH2Ph), followed by hydrogenation to liberate the free guanidine, which underwent an intramol. SN2 reaction to form the tetrahydropyrimidine ring B of VIII. Further hydrogenation reduced the ketone to yield 42% of VIII containing the fully functionalized tricyclic system and protected hydroxymethyluracil side chain of cylindrospermopsin. Hydrolysis of the pyrimidine in concentrated hydrochloric acid and selective monosulfation completed the synthesis of cylindrospermopsin. In the experiment, the researchers used many compounds, for example, 2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1Recommanded Product: 59864-30-1).
2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1) belongs to pyrimidine derivatives. Pyrimidines are isomeric with two other forms of diazines: pyridazine, with the nitrogen atoms in the 1 and 2 positions; and pyrazine, with the nitrogen atoms in the 1 and 4 positions. For example, the neurotoxin tetrodotoxin is a pyrimidine derivative. It is found in a number of species including the Japanese puffer fish, the blue-ringed octopus, and the orange-bellied newt. Tetrodotoxin prevents the transmission of nerve signals and can result in paralysis and death.Recommanded Product: 59864-30-1
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia