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Synthesis 2017; 49(21): 4869-4875
DOI: 10.1055/s-0036-1590799
DOI: 10.1055/s-0036-1590799
paper
Short and Diastereoselective Total Synthesis of the Polyhydroxylated Pyrrolidine LAB-1: A Potent α-Glycosidase Inhibitor
E.C.S. thanks São Paulo Research Foundation (FAPESP) for a fellowship (process #2013/06757-6). F.C. thanks FAPESP for financial support (process #2013/07600-3 and 2013/10449-5). A. A. Dos Santos thanks FAPESP for financial support (process # 2016/09579-0); F.C. thanks also the National Council for Scientific and Technological Development (CNPq) for a research fellowshipWeitere Informationen
Publikationsverlauf
Received: 21. Mai 2017
Accepted after revision: 24. Mai 2017
Publikationsdatum:
27. Juli 2017 (online)
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 α-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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590799.
- Supporting Information
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Some years ago, we have described an experimental protocol for the MBH reaction with a chiral α-aminoaldehyde, where no racemization was observed. Unfortunately, this result was revealed to be not so robust, see: