| Full text | |
| Author(s): |
Vasconcelos, Stanley N. S.
[1]
;
de Oliveira, Isadora Maria
[2]
;
Shamim, Anwar
[2]
;
Zukerman-Schpector, Julio
[3]
;
Pimenta, Daniel C.
[4]
;
Stefani, Helio A.
[1, 2]
Total Authors: 6
|
| Affiliation: | [1] Univ Sao Paulo, Fac Ciencias Farmaceut, Dept Farm, Sao Paulo, SP - Brazil
[2] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, Sao Paulo, SP - Brazil
[3] Univ Fed Sao Carlos, Dept Quim, Sao Carlos, SP - Brazil
[4] Inst Butantan, Sao Paulo, SP - Brazil
Total Affiliations: 4
|
| Document type: | Journal article |
| Source: | ADVANCED SYNTHESIS & CATALYSIS; v. 361, n. 18 JULY 2019. |
| Web of Science Citations: | 1 |
| Abstract | |
The steroselective oxa-Michael addition of the phenol moiety present in tyrosine and 3-iodotyrosine to different propargyl aldehydes delivered products with predominantly Z stereochemistry, as evidenced by X-ray crystallography analysis. When ethyl propiolate was used as the propargyl ester source, the products were achieved with exclusively E stereochemistry with yields ranging from 17% to 91%. The oxa-Michael addition compounds served as substrates in the synthesis of 5- and 6-membered heterocyclic compounds. The atmosphere applied to the reaction medium directly influenced the formation of the products. When an inert atmosphere of nitrogen was applied, a 2-aryl-3-formyl-5-alanylbenzofuran core was selectively obtained via a Heck intramolecular reaction, while the reactions carried out under a carbon monoxide atmosphere led exclusively to 6-alanyl-2-arylflavone derivatives via reductive intramolecular acylation. (AU) | |
| FAPESP's process: | 13/17960-7 - Functionalization of 3-iodo-(L)-Tyrosine via Suzuki-Miyaura Reaction Using Potassium Organotrifluoroborate salts |
| Grantee: | Stanley Nunes Siqueira Vasconcelos |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 16/04289-3 - Synthesis of calcogeno amino acids derivatives and 4-calcogeno quinolines via multicomponent reactions |
| Grantee: | Isadora Maria de Oliveira |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |