A new concise synthesis of nectrisine and its facile conversion to phosphonoazasugars

The synthesis of new sugar-derived phosphonic acids from protected nectrisine is described. The key step is a highly stereoselective addition of a phosphonate anion to a sugar-derived dihydropyrrole to provide a versatile synthetic intermediate which can be functionalised in multiple ways. The synth...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 45; pp. 7949 - 7952
Main Authors Bosco, Michaël, Bisseret, Philippe, Bouix-Peter, Claire, Eustache, Jacques
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 05.11.2001
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNGUS
INHIBITORS
ANALOGS
STEREOSELECTIVE SYNTHESIS
1-PHOSPHATE
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Summary:The synthesis of new sugar-derived phosphonic acids from protected nectrisine is described. The key step is a highly stereoselective addition of a phosphonate anion to a sugar-derived dihydropyrrole to provide a versatile synthetic intermediate which can be functionalised in multiple ways. The syntheses of nectrisine and new sugar-derived phosphonates (B, C, D) from the common advanced intermediate A are described.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)01684-7