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

Author(s)

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

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

• 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 type: Scholarships in Brazil - Doctorate
• 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
• 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