Synthesis of [3.3.0] bicyclic isoxazolidinyl nucleosides
✍ Scribed by Yuejun Xiang; Raymond F. Schinazi; Kang Zhao
- Book ID
- 104364604
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 216 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0960-894X
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✦ Synopsis
The isoxazolidine derivative 6, prepared from an intermolecular 1,3dipolar cyeloaddition of the (5S)-unsaturated lactone 5 and N-methylnitrone, was effectively used for the synthesis of [3.3.0] bicyclic isoxazolidinyl cytidine 4a and thymidine 4b.
📜 SIMILAR VOLUMES
## Abstract Starting with 5‐iodo N,O‐nucleosides, prepared by 1,3‐dipolar cycloaddition of nitrones with vinyliodouracil, or vinyl acetate followed by coupling with silylated iodouracil, a series of 5‐alkynyl N,O‐nucleosides were synthesized via a palladium‐catalyzed (Sonogashira) coupling reaction
Stereoselective rearrangement of 6,7-epoxy-3-oxabicyclo[3.2.0]heptan-2-ones 2 and 3 in water afforded a cisfused butyrolactone as a mixture of two epimers 1a-b. These were used as the starting materials to prepare new bicyclonucleosides 8a-b.