| Full text | |
| Author(s): |
Total Authors: 4
|
| Affiliation: | [1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
|
| Document type: | Journal article |
| Source: | Journal of Organic Chemistry; v. 79, n. 14, p. 6748-6753, JUL 18 2014. |
| Web of Science Citations: | 15 |
| Abstract | |
A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an alpha,beta-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a {[}1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines. (AU) | |
| FAPESP's process: | 10/18801-1 - DIVERGENT SYNTHESIS OF PYRROLIDINE ALKALOIDS FROM ALFA,BETAUNSATURATED DIAZOKETONES AS BIFUNCTIONAL REAGENTS. APPLICATION IN THE TOTAL SYNTHESIS OF (±)-PREUSSIN |
| Grantee: | Isac George Rosset |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 12/04685-5 - New synthetic methodologies for the construction of pyrrolidine, piperidine and indolizidine systems |
| Grantee: | Antonio Carlos Bender Burtoloso |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 08/09653-9 - Total syntheses of the cardiotonics pumiliotoxin 209 F and homopumiliotoxin 223 G |
| Grantee: | Vagner Dantas Pinho |
| Support Opportunities: | Scholarships in Brazil - Doctorate |