D-rybono-1,4-lakton. Część II. Wykorzystanie w syntezie organicznej - wybrane reakcje

Janusz Madaj , Justyna Samaszko-Fiertek , Rafał Ślusarz , Barbara Dmochowska

Abstract

There are many examples of syntheses with d-ribono-1,4-lactone as a substrate. Among all, its biggest advantage is undoubtedly its accessibility. It can be synthesized on a large scale from naturally available raw materials. Its characteristic feature is the stable configuration of individual carbon atoms in multiple reaction conditions. Very important is the presence of a carbonyl moiety, allowing for a variety of additions which is crucial for carbon-carbon bond formation, the most difficult synthesis in organic chemistry. In this article we present selected examples of articles that were published after 1984. In this year, the second article describing the Use of d-Ribonolactone in Organic Synthesis [36] was published. After this time many articles describing the use of the entitled lactone as a substrate in organic synthesis were published. We thought it would be worthwhile to present in Polish a selection of them. C-Glycosides and nucleoside analogs are a particularly important type of synthesized products. Examples of their synthesis are presented in this work, namely, neplanocin A [5], B [31] and F [24], citreovirdin [14], 2-bromopyridin α- and β-d-ribofuranosides [10], 4-deazaformicin A [27] and varitriol [ 33].
Author Janusz Madaj PChC
Janusz Madaj,,
- Laboratory of Carbohydrate Chemistry
, Justyna Samaszko-Fiertek PChC
Justyna Samaszko-Fiertek,,
- Laboratory of Carbohydrate Chemistry
, Rafał Ślusarz PChC
Rafał Ślusarz,,
- Laboratory of Carbohydrate Chemistry
, Barbara Dmochowska PChC
Barbara Dmochowska,,
- Laboratory of Carbohydrate Chemistry
Other language title versionsD-ribono-1,4-lactone. Part II. Use in organic synthesis - selected reactions
Journal seriesWiadomości Chemiczne, ISSN 0043-5104, e-ISSN 2300-0295
Issue year2017
Vol71
No11-12
Pages861-885
Publication size in sheets1.2
Keywords in PolishD-rybono-1,4-lakton, C-glikozydy, analogi nukleozydów, neplanocyna
Keywords in EnglishD-ribono-1,4-lactone, C-glycosides, nucleosides analogs, neplanocin
URL http://www.dbc.wroc.pl/dlibra/docmetadata?id=39719
Languagepl polski
LicenseOther; published final; Other open licence; with publication
Score (nominal)7
ScoreMinisterial score = 7.0, 26-02-2018, ArticleFromJournal
Ministerial score (2013-2016) = 7.0, 26-02-2018, ArticleFromJournal
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