Author
C. Booma
Bio: C. Booma is an academic researcher. The author has contributed to research in topics: Aldose & Ferrier rearrangement. The author has an hindex of 1, co-authored 1 publications receiving 23 citations.
Topics: Aldose, Ferrier rearrangement, Glycal
Papers
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TL;DR: In this paper, the synthesis of tri-O-benzyl-2-C-acetoxymethyl glycals and subsequent Ferrier rearangement to give 2C-methylene glycosides is described.
Abstract: Syntheis of tri-O-benzyl-2-C-acetoxymethylglycals and subsequent Ferrier rearangement to give 2-C-methylene glycosides is described.
24 citations
Cited by
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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
TL;DR: An efficient approach for the synthesis of a variety of C-aryl and spiro-C-aryl glycosides is described, which relies on a sequential enyne metathesis to generate the 1,3-diene moiety and Diels-Alder reaction with different dienophiles followed by aromatisation.
Abstract: An efficient approach for the synthesis of a variety of C-aryl and spiro-C-aryl glycosides is described. This diversity-oriented strategy employed here relies on a sequential enyne metathesis to generate the 1,3-diene moiety and Diels–Alder reaction with different dienophiles followed by aromatisation. Whereas cross-enyne metathesis with ethylene gas is used to install the 1,3-diene moiety at the anomeric centre for the synthesis of C-aryl glycosides, an intramolecular enyne metathesis on the sugar enyne is performed to generate the 1,3-diene moiety for the synthesis of spiro-C-aryl glycosides. Efforts to extend this strategy to the synthesis of the core structure of natural C-aryl glycoside gilvocarcin are also described. A combination of both C-aryl and spiro-C-aryl glycosides in the same moiety to combine the features thereof has also been accomplished. A tandem enyne metathesis/Diels–Alder reaction/aromatisation has also been attempted to directly access the C-aryl glycosides in one pot albeit in low yield.
56 citations
TL;DR: The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics, and 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a d-glucal-derived gem-dihalocyclopropanated sugar.
Abstract: The conversion of cyclopropane-fused carbohydrates into oxepines is an attractive method for accessing diverse members of the septanoside family of carbohydrate mimetics. 2-Bromooxepines are obtained through silver(I)-promoted thermal ring expansion of a d-glucal-derived gem-dihalocyclopropanated sugar. In contrast, cyclopropane ring cleavage under basic conditions leads to 2-C-branched pyranosides, not the 2-bromooxepine structures assigned in an earlier report.
49 citations
TL;DR: In this article, a new class of 2-C-formyl glycals, incorporating an α,β-unsaturated carbonyl system, have been proposed as potential synthons for numerous organic transformations.
44 citations
TL;DR: In this paper, C-2-Methylene O- and C-glycosides are readily synthesized from C-acetoxymethyl glycals using Nafion-H®, montmorillonite K-10, LiClO4 (0.07m) in dichloromethane and Pd(PPh3)4 as catalysts.
38 citations