Journal ArticleDOI
Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations.
Elumalai Kumaran,Meenakshisundaram Santhi,Kalpattu K. Balasubramanian,Shanmugasundaram Bhagavathy +3 more
TLDR
Reaction of 2-C-hydroxymethyl-d-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2, 6-dimmethylphenol, which led to totally unexpected transformations.About:
This article is published in Carbohydrate Research.The article was published on 2011-09-27. It has received 12 citations till now. The article focuses on the topics: Ferrier rearrangement & Ferrier carbocyclization.read more
Citations
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Journal ArticleDOI
Recent Developments in the Ferrier Rearrangement
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.
Journal ArticleDOI
Applications of 2-C-Formyl-Glycals in Organic Synthesis
TL;DR: Recent developments in the synthesis and applications of 2-C-formyl-glycals, the versatile chiral intermediates, are summarized in this review.
Journal ArticleDOI
Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals
TL;DR: In this paper, a method to obtain enantiomerically pure 8-oxabicyclo[3.2.1] octanes via gold-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement of glycal derived 1,6-enyne bearing propargylic carboxylates is described.
Journal ArticleDOI
ZnBr2-Catalyzed and Microwave-Assisted Synthesis of 2,3-Unsaturated Glucosides of Hindered Phenols and Alcohols
TL;DR: In this paper, the Ferrier reaction of hindered phenols and alcohols was used to obtain α-2,3-unsaturated glucoside acetates in good yields and with good stereoselectivity.
Journal ArticleDOI
Diastereoselective Synthesis of C-Vinyl Glycosides via Gold(I)-Catalyzed Tandem 1,3-Acyloxy Migration/Ferrier Rearrangement
TL;DR: A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate.
References
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Target-oriented and diversity-oriented organic synthesis in drug discovery.
TL;DR: Several synthetic planning principles for diversity-oriented synthesis and their role in the drug discovery process are presented in this review.
Journal ArticleDOI
The Migrastatin Family: Discovery of Potent Cell Migration Inhibitors by Chemical Synthesis
Christoph Gaul,Jon T. Njardarson,Dandan Shan,David C. Dorn,Kai Da Wu,William P. Tong,Xin-Yun Huang,Malcolm A.S. Moore,Samuel J. Danishefsky,Samuel J. Danishefsky +9 more
TL;DR: Utilizing the power of diverted total synthesis (DTS), a series of otherwise inaccessible analogues was prepared and evaluated for their potential as tumor cell migration inhibitors in several in vitro assays, presenting macrolactones 45 and 48, as well asmacrolactam 55, macroketone 60, and CF(3)-alcohol 71 as promising anti-metastatic agents.
Book ChapterDOI
Substitution-with-Allylic-Rearrangement Reactions of Glycal Derivatives
TL;DR: Glycals (or usually their O-substituted derivatives) are readily converted into 2,3-unsaturated glycosyl compounds with O-, C-, N-, S- or otherwise linked substituents at the anomeric position as discussed by the authors.
Journal ArticleDOI
Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides†
TL;DR: In this article, tri-O-acetyl-d-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity.