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Nitrile oxide cycloadditions to olefinated sugars

✍ Scribed by Pedro A Colinas; Volker Jäger; Albrecht Lieberknecht; Rodolfo D Bravo

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
265 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Carbohydrate derivatives with a spiro-isoxazoline moiety as present in psammaplysins and ceratinamides (metabolites isolated from marine sponges) were prepared in good yields and excellent regio-and diastereoselectivity by a route involving Wittig olefination and 1,3-dipolar cycloaddition as key steps.

📜 SIMILAR VOLUMES

Sugar-based ethenyl ethers: stereoselect
Sugar-based ethenyl ethers: stereoselective dipolar cycloadditions of nitrile oxides
✍ Matthieu Desroses; Florence Chéry; Arnaud Tatibouët; Ottorino De Lucchi; Patrick 📂 Article 📅 2002 🏛 Elsevier Science 🌐 English ⚖ 233 KB

Selected sugar-based ethenyl ethers have been employed in 1,3-dipolar cycloaddition with nitrile oxides. In the D-fructo series, high diastereoselectivity was observed as compared with the 3-epimeric D-psico series.

Cycloadditions of Nitrile Oxides to Itac
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✍ Svêtlík, Jan ;Liptaj, Tibor ;Hanuš, Vladimír 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 294 KB

## Abstract New spiro heterocycles, 1‐oxa‐2,7‐diazaspiro[4.4]non‐2‐ene‐6,8‐diones 3a–c and 8a, c were obtained in the reaction of itaconimides 1a–c with nitrile oxides 2 and 7.