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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.)

Three-Step Synthesis of (+)-Preussin from Decanal

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Rosset, Isac G. [1] ; Dias, Rafael M. P. [1] ; Pinho, Vagner D. [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 4
[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

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 type: 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 type: 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 type: Scholarships in Brazil - Doctorate