The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane(SMILESS: C1(CC2=N[C@@H](C3=CC=CC=C3)CO2)=N[C@@H](C4=CC=CC=C4)CO1,cas:132098-59-0) is researched.Quality Control of Bis((S)-4-phenyl-4,5-dihydrooxazol-2-yl)methane. The article 《Enantioselective Total Synthesis of (-)-Acutumine》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:132098-59-0).
An account of the total synthesis of the tetracyclic alkaloid (-)-acutumine (I) is presented. A first-generation approach to the spirocyclic subunit was unsuccessful as a result of incorrect regioselectivity in a radical cyclization. However, this work spawned a second-generation strategy in which the spirocycle was fashioned via a radical-polar crossover reaction. This process merged an intramol. radical conjugate addition with an enolate hydroxylation and created two stereocenters with excellent diastereoselectivity. The reaction was promoted by irradiation with a sunlamp, and a ditin reagent was required for aryl radical formation. These facts suggest that the substrate may function as a sensitizer, thereby facilitating homolytic cleavage of the ditin reagent. The propellane motif of the target was then installed via annulation of a pyrrolidine ring onto the spirocycle. The sequence of reactions used included a phenolic oxidation, an asym. ketone allylation mediated by Nakamura’s chiral allylzinc reagent, an anionic oxy-Cope rearrangement, a one-pot ozonolysis-reductive amination, and a Lewis acid promoted cyclization of an amine onto an α,β-unsaturated di-Me ketal. Further studies of the asym. ketone allylation demonstrated the ability of the Nakamura reagent to function well in a mismatched situation. A TiCl4-catalyzed regioselective Me enol etherification of a 1,3-diketone completed the synthesis.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles