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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.)

Short and Diastereoselective Total Synthesis of the Polyhydroxylated Pyrrolidine LAB-1: A Potent -Glycosidase Inhibitor

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Author(s):
da Silva, Erica C. [1] ; Yamakawa, Nathalia C. G. [1] ; Dos Santos, Alcindo A. [2] ; Coelho, Fernando [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, Lab Synth Nat Prod & Drugs, POB 6154, BR-13083970 Campinas, SP - Brazil
[2] Univ Sao Paulo, Inst Chem, Ave Prof Lineu Prestes, 748, Cidade Univ, BR-05508000 Sao Paulo, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: SYNTHESIS-STUTTGART; v. 49, n. 21, p. 4869-4875, NOV 2017.
Web of Science Citations: 3
Abstract

We described herein a total synthesis of 1,4-dideoxy-1,4-imino-l-arabinitol {[}(2S,3S,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol, LAB-1], a polyhydroxylated pyrrolidine, which has been demonstrated to be a selective and potent -glycosidase inhibitor. The main features of our approach are its shortness, efficiency, and simplicity. The total synthesis was accomplished in 6 steps with an overall yield of 12%, starting from a chiral optically active Morita-Baylis-Hillman (MBH) adduct prepared (without epimerization), from Garner's aldehyde. As far as we know, this is the first report describing the total synthesis of this biologically active pyrrolidine by exploring the synthetic versatility of a MBH adduct. (AU)

FAPESP's process: 13/10449-5 - Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest
Grantee:Fernando Antonio Santos Coelho
Support Opportunities: Regular Research Grants
FAPESP's process: 13/06757-6 - Synthesis and biological evaluation of functionalized pyrrolidines and piperidines having potential inhibitory activity against alpha-glycosidase, from Morita-Baylis-Hillman adducts
Grantee:Érica Cristina da Silva
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 16/09579-0 - Synthesis of Organic Selenides and Tellurides for Detection and Interception of Endogenous Oxidants
Grantee:Alcindo Aparecido dos Santos
Support Opportunities: Regular Research Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC