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Deoxyhydantocidin: Synthesis by Base-Catalyzed Spiro Cyclization and Interconversion with the 1′-Epimer (2000)

Renard, Annabelle ; Kotera, Mitsuharu ; Brochier, Marie-Christine ; [et al.]

Weinheim : Wiley-Blackwell

Liebigs Annalen 2000 (2000), S. 1831-1840

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ISSN: 1434-193X

Keywords: Cyclizations ; Spiro compounds ; Nucleosides ; Isomerizations ; Chemistry ; General Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: ---Syntheses of the spiro nucleosides 2′-deoxyhydantocidin 3a and its 1′-epimer 3b are described. The newly developed route involves a Horner-Wadsworth-Emmons condensation of the phosphonate 16 with the erythrose derivative 15 affording a mixture of six isomers which was fully assigned by NMR spectroscopy. The mixture was directly converted into the final compounds in an efficient base-catalyzed cyclization reaction. A base-catalyzed interconversion between the two isomers was observed.

Additional Material: 2 Ill.

Type of Medium: Electronic Resource

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