| Full text | |
| Author(s): |
Bernardi Rosso, Giovanni
;
Matos Paz, Bruno
;
Aloise Pilli, Ronaldo
Total Authors: 3
|
| Document type: | Journal article |
| Source: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2022, n. 28, p. 6-pg., 2022-07-27. |
| Abstract | |
The structure proposed for the putative Stemona alkaloid named as parvistemoamide (4 a or 4 b) has been questioned after revising the literature data and an attempted preparation of structure 4 a, which led to a 5 : 1 mixture of (+/-)-stemoamide (1). Studies on the intramolecular Friedel-Crafts alkylation of a furan 12 containing a Z double bond tethered to a precursor of a N-acyliminium ion are reported. As shown for bromo substituted furan 31, the cyclization occurred when a 4-carbon saturated tether was present, allowing for the formal syntheses of racemic tuberostemospiroline (2) and stemona-lactam R (3). (AU) | |
| FAPESP's process: | 19/13104-5 - Planning and synthesis of inhibitors based on biological targets: the case of neglected kinases |
| Grantee: | Ronaldo Aloise Pilli |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 18/05742-9 - Organocatalytic Approaches to the Enantioselective Synthesis of Stemona Alkaloids |
| Grantee: | Bruno Matos Paz |
| Support Opportunities: | Scholarships in Brazil - Post-Doctoral |