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Author

Fernando Lobo

Other affiliations: University of La Laguna
Bio: Fernando Lobo is an academic researcher from Spanish National Research Council. The author has contributed to research in topics: Ferrier rearrangement & Allylic rearrangement. The author has an hindex of 5, co-authored 15 publications receiving 177 citations. Previous affiliations of Fernando Lobo include University of La Laguna.

Papers
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Journal ArticleDOI
TL;DR: A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.

121 citations

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TL;DR: O-Ethylation of phthalides with Meerwein's reagent followed by reaction of the ensuing salts with pyrrole, results in the formation of 5-alkoxy-5-phenyl dipyrromethane derivatives, which function as ready precursors of ortho-substituted 8-aryl BODIPY derivatives by reaction with borontrifluoride etherate.
Abstract: O-Ethylation of phthalides with Meerwein’s reagent followed by reaction of the ensuing salts with pyrrole, results in the formation of 5-alkoxy-5-phenyl dipyrromethane derivatives, which function as ready precursors of ortho-substituted 8-aryl BODIPY derivatives by reaction with borontrifluoride etherate, an overall process that can be carried out in a one-pot operation.

22 citations

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TL;DR: Compounds resulting from ring expansion (oxepanes), ring contraction (tetrahydrofurans), or branched pyranoses, by incorporation of nucleophiles, can be obtained from 6-O-benzyl, 6-hydroxy, or 6-Silyl derivatives, respectively.
Abstract: Novel substrates that combine dicobalt hexacarbonyl propargyl (Nicholas) and pyranose-derived allylic (Ferrier) cations have been generated by treatment of hexacarbonyldicobalt (C-1)-alkynyl glycals with BF3 (.) Et2 O. The study of these cations has resulted in the discovery of novel reaction pathways that have shown to be associated to the nature of O-6 substituent in the starting alkynyl glycals. Accordingly, compounds resulting from ring expansion (oxepanes), ring contraction (tetrahydrofurans), or branched pyranoses, by incorporation of nucleophiles, can be obtained from 6-O-benzyl, 6-hydroxy, or 6-O-silyl derivatives, respectively. The use of a 6-O-allyl alkynyl glycal led to a suitable funtionalized oxepane able to experience an intramolecular Pauson-Khand cyclization leading to a single tricyclic derivative.

19 citations

Journal ArticleDOI
TL;DR: In this paper, recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals are discussed.
Abstract: Review: recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals; <250 refs.

18 citations

Journal ArticleDOI
TL;DR: The aim of this review is to highlight the rich chemistry of ∆-2,3 unsaturated pyranosides, emphasizing the variety of transformations that have been carried out in these substrates during the last decade.
Abstract: Unsaturated carbohydrate derivatives are useful intermediates in synthetic transformations leading to a variety of compounds. The aim of this review is to highlight the rich chemistry of ∆-2,3 unsaturated pyranosides, emphasizing the variety of transformations that have been carried out in these substrates during the last decade.

16 citations


Cited by
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Journal ArticleDOI
TL;DR: This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter.
Abstract: Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

194 citations

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182 citations

Journal ArticleDOI
TL;DR: This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.
Abstract: This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes. A classification of the preparative routes to these synthetic targets according to methodologies and compound categories is provided. Several of these compounds, regardless of their natural or synthetic origin, display antidiabetic properties due to enzyme inhibition (glycogen phosphorylase, protein tyrosine phosphatase 1B) or by inhibiting renal sodium-dependent glucose cotransporter 2 (SGLT2). The latter class of synthetic inhibitors, very recently approved as antihyperglycemic drugs, opens new perspectives in the pharmacological treatment of type 2 diabetes. Various compounds with the C-glycopyranosyl (het)arene motif were subjected to biological studies displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.

151 citations

Journal ArticleDOI
TL;DR: This review highlights the C-glycosylation methods that have been practised in the total synthesis of natural products and pharmaceuticals in the past decade.
Abstract: Chemical C-glycosylation has been well developed to improve stereoselectivity in recent years. Due to its high efficiency to build C-glycosides or O-cyclic compounds, C-glycosylation has found widespread use in the synthesis of biologically active molecules. This review highlights the C-glycosylation methods that have been practised in the total synthesis of natural products and pharmaceuticals in the past decade.

75 citations

Journal ArticleDOI
TL;DR: In the last few years, considerable progress has been made in the synthesis of C-glycosides as mentioned in this paper, and due to its versatility, C glycosides play a pivotal role in developing novel materials, surfactants and bioactive molecules.

69 citations