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Mild Stereoselective Synthesis of Fully Protected 1,6-Dioxaspiro[4.5]dec-3-ene Derivatives of Sugars

✍ Scribed by Romualdo Caputo; Annalisa Guaragna; Giovanni Palumbo; Silvana Pedatella; Francesco Solla


Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
221 KB
Volume
2002
Category
Article
ISSN
1434-193X

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A synthesis of 1,6-dioxaspiro[4.5]dec-3-
✍ Richard Whitby; Philip KocieΕ„ski πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 205 KB

Base-catalysed rearrangement of a 2-alkynyl-tetrahydropyran generates an allenol ether intermediate which undergoes acid-catalysed cyclisation to the 1,6-dioxaspiro[4S]dec-3-ene system. We recently described a synthesis of the 1,7-dioxaspiro[5S]undec-4-ene system (4)' which made strategic use of th