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Issue 5, 2005
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Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: new insights into glycal reactivity

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Abstract

An efficient, enantioselective synthesis of erythro-4-deoxyglycals has been developed using asymmetric aldehyde allylation and tungsten-catalyzed alkynol endo-cycloisomerization as the key steps. These versatile synthetic scaffolds have been elaborated to a variety of products using stereoselective transformations that are complementary to those available using the corresponding threo glycals. This work has provided valuable insights into the relationships between glycal structure and reactivity. In addition, a new diene-forming side reaction during tungsten-catalyzed alkynol cycloisomerization has been discovered.

Graphical abstract: Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: new insights into glycal reactivity

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Publication details

The article was received on 18 Nov 2004, accepted on 14 Dec 2004 and first published on 24 Jan 2005


Article type: Paper
DOI: 10.1039/B417429A
Citation: Org. Biomol. Chem., 2005,3, 798-803
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    Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- and diversity-oriented synthesis: new insights into glycal reactivity

    S. B. Moilanen and D. S. Tan, Org. Biomol. Chem., 2005, 3, 798
    DOI: 10.1039/B417429A

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