| Full text | |
| Author(s): |
Castro, Joaquim A. M.
;
Serikava, Bruno K.
;
Naciuk, Fabricio F.
;
Ligiero, Carolina B. P.
;
Morgon, Nelson H.
;
Miranda, Paulo C. M. L.
Total Authors: 6
|
| Document type: | Journal article |
| Source: | CHEMISTRYSELECT; v. 8, n. 17, p. 7-pg., 2023-02-24. |
| Abstract | |
An elongated resonance with the N-oxide group and the vinylogous effect of the oxoammonium group allowed the regioselection switch during an oxidative amination reaction of an isoquinolinedione, permitting us to prepare isocaulibugulones A, B, C, and D in a straightforward approach. The alkaloid counterparts A and D were synthesized in 4 steps with 11-36 % global yield. A further late-stage halogenation step at isocaulibugulone A led to preparing counterparts B and C with 83-94 % yield. Density Functional Theory (DFT) calculations anticipate the effects mentioned above and the disruptive action of hydrogen bonding in the process, which were observed experimentally in the synthesis of isocaulibugulone D due to the partial loss of regioselectivity. (AU) | |
| FAPESP's process: | 16/10498-4 - Investigation of strategies of adaptation to the pathogenic life style of fungi from the Moniliophthora genus at various levels of biological organizations: species, biotypes, and geographic lineages |
| Grantee: | Antonio Vargas de Oliveira Figueira |
| Support Opportunities: | Research Projects - Thematic Grants |
| 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 |