Preparation of 2 '-Deoxy-2 '-spirocyclopropylcytidine via an Alternative Cyclopropanation Reaction

Lemaire, Sebastien; Diene, Coura; Gavryushin, Andrei; Du Jourdin, Xavier Mollat; Paolini, Lea; Jusseau, Xavier; Knochel, Paul and Farina, Vittorio (2019): Preparation of 2 '-Deoxy-2 '-spirocyclopropylcytidine via an Alternative Cyclopropanation Reaction. In: Journal of Organic Chemistry, Vol. 84, No. 8: pp. 4910-4914

Abstract

Herein we report the preparation of 2'-deoxy2'-spirocyclopropylcytidine via an alternative cyclopropanation reaction starting from gamma-silyl tertiary alcohols. Activation of the hydroxyl function with thionyl chloride in the presence of 4-DMAP allows the ring-closing step under mild conditions. Participation of the uracil moiety in the cyclization step is proposed.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0022-3263
• Language: English