A mild and efficient stereoselective synthesis of hexacyclic indole alkaloids with a tetrahydro-β-carboline motif has been developed by utilizing the Pictet-Spengler reaction and tandem N-acylation followed by intramolecular Diels-Alder cyclization. Initially, a diene unit was installed in the tetrahedron β-carboline skeleton through Pictet-Spengler cyclization of the corresponding aldehyde with tryptophan ester. The dienophile moiety was introduced by N-acylation of tetrahydro-β-carboline. Successive, in situ, [4 + 2] intramolecular Diels-Alder cycloaddition of the activated dienophile and conjugated diene containing intermediate furnished bridged polycyclic heterocycles with high diastereoselectivity. Formation of four new rings, five new covalent bonds, and five new chiral centers with excellent stereoselectivity is the key feature of this strategy. The diastereoselective formation of product was attributed to intramolecular chirality transfer through a chiral amino acid. The stereoselective outcome of this tandem reaction was confirmed by X-ray crystallographic studies. The developed synthetic strategy was also explored on a soluble polymer support to incorporate the advantage of rapid synthesis and a high-throughput workup process toward the development of a green synthetic protocol for polycyclic alkaloids.
Bifunctional SBA-1 mesoporous silica nanoparticles (MSNs) with carboxylic acid and amino groups (denoted as CNS-10-10) have been successfully synthesized, characterized, and employed as adsorbents for dye removal. Adsorbent CNS-10-10 shows high affinity towards cationic and anionic dyes in a wide pH range, and exhibits selective dye removal of a two-dye mixture system of cationic methylene blue and anionic eosin Y. By changing the pH of the medium, the selectivity of the adsorption behavior can be easily modulated. For comparison purposes, the counterparts, that is, pure silica SBA-1 MSNs (CS-0) and those with either carboxylic acid or amino functional groups (denoted as CS-10 and NS-10, respectively) were also prepared to evaluate their dye-adsorption behaviors. As revealed by the zeta-potential measurements, the electrostatic interaction between the adsorbent surface and the dye molecule plays an important role in the adsorption mechanism. Adsorbent CNS-10-10 can be easily regenerated and reused, and maintains its adsorption efficiency up to 80 % after four cycles.
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