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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Straightforward Synthesis of Isoellipticine by Palladium-Catalysed Coupling Reactions

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Author(s):
Naciuk, Fabricio F. [1, 2] ; Castro, Joaquim A. M. [1] ; Serikava, Bruno K. [1] ; Miranda, Paulo C. M. L. [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP - Brazil
[2] CNPEM, LNBio, Brazilian Ctr Res Energy & Mat, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: CHEMISTRYSELECT; v. 3, n. 2, p. 436-439, JAN 17 2018.
Web of Science Citations: 2
Abstract

Our novel synthetic route to isoellipticine featured palladium-catalyzed intramolecular reactions for the construction of the B ring of the pyridocarbazole nucleus. The adequate palladium-catalyzed reaction depended upon the oxidation conditions that were applied in order to prepare the immediate synthetic precursor. When CAN was used to make the quinone intermediate, an oxidative cyclization through a double C-H bond activation was applied. Conversely, when the oxidation condition involved TCCA as oxidant, a direct C-H arylation was employed. Both approaches showed similar efficiencies in order to construct the pyridocarbazole nucleus. Isoellipticine was prepared in only 5 steps with a 21%-23% overall yield. (AU)

FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
Grantee:Carlos Roque Duarte Correia
Support Opportunities: Research Projects - Thematic Grants