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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.)

alpha,beta-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D

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Author(s):
Bernardim, Barbara [1] ; Pinho, Vagner D. [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 3
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. 77, n. 21, p. 9926-9931, NOV 2 2012.
Web of Science Citations: 25
Abstract

A versatile and concise approach for the stereoselective synthesis of mono-, di-, and trihydroxylated indolizidines is presented in four to six steps from Cbz-prolinal and a diazophosphonate. The key steps involved a Wolff rearrangement, followed by a stereoselective dihydroxylation/epoxidation reaction, from an alpha,beta-unsaturated diazoketone. The strategy also permits extension to the synthesis of many natural hydroxylated indolizidine alkaloids as demonstrated in the formal synthesis of pumiliotoxin 251D. (AU)

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