Unsaturated Sugars

Ferrier, R. J.

doi:10.1016/s0065-2318(08)60351-0

Cited by 212 publications

(27 citation statements)

References 173 publications

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“…Rearrangement of the enollactone 132 to a cyclopentanone derivative 134. a) LiAlH(OtBu) 3 such as glycals [57], which are by far the most commonly unsaturated carbohydrate derivatives and have been proven valuable starting materials in a large variety of synthetic endeavors. Similar to the endocyclic unsaturated derivatives, the exocyclic unsaturated derivatives are also studied extensively.…”

Section: Conversion Of Exocyclic-olefinic Fura-nosides or Pyranosidesmentioning

confidence: 99%

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Zhou¹,

Wang²,

Zhang³

et al. 2006

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As the structural constituents of many naturally occurring molecules, synthesis of functionalized carbocyclic derivatives has been widely investigated. Among numerous approaches to construct carbocyclic compounds, there is an efficient way of forming carbocyclic derivatives by the use of various monosaccharides as chiral building blocks. In this review, synthetic conversions to functionalized carbocyclic compounds from exocyclic-olefinic saccharides and their applications to synthesis of some natural products or natural product-like analogues will be discussed. The emphases will be put on the latest methodology developments of ring-conversion rearrangement reactions catalyzed by metal catalysts.

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Section: Conversion Of Exocyclic-olefinic Fura-nosides or Pyranosidesmentioning

confidence: 99%

From Exocyclic-Olefinic Carbohydrate Derivatives to Functionalized Carbocyclic Compounds

Zhou¹,

Wang²,

Zhang³

et al. 2006

COC

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“…However, it was the work of Ferrier and Prasad, depicted in Scheme 1, that rendered the process, 1 3, available on a preparative scale [5]. This reaction has come to be known as the Ferrier I rearrangement, and the cationic intermediate, 2, has played a relevant role in many carbohydrate transformations [6,7]. Almost simultaneously, the reductive elimination of vicinal disulfonates, e.g.…”

Section: Introductionmentioning

confidence: 99%

Unsaturated Sugars: A Rich Platform for Methodological and Synthetic Studies

Fraser‐Reid¹,

López²

2009

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“…This reaction should take place under mild conditions in order to provide preference over the Ferrier rearrangement, which is a competing reaction. 11 Successful direct addition can be accomplished in the presence of several catalysts, for instance, triphenylphosphine-hydrogen bromide (TPHB), 12 cation-exchange resin Dowex AG 50WX2, 13 BCl 3 , BBr 3 , 14 CAN 15 or the CeCl 3 -NaI reagent system. 16 According to these procedures, 2-deoxy-a-glycosides are formed as the major products.…”

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confidence: 99%

“…Significant predominance of the a anomer was seen when glycal 3 with a bulky group at the C-3 position was applied in reactions with glycerol derivatives 8 and 9 (Table 1, entries [11][12]. Glycoglycerolipids 23 and 24 were formed as the predominant 2-deoxy-a-L Lglycosides (a:b = 15:1) showing the superiority of glycal 3 over the perbenzylated glycal 2.…”

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confidence: 99%