Article: Regio- and Stereoselective Synthesis of C-4′ Spirocyclobutyl Ribofuranose Scaffolds and Their Use as Biologically Active Nucleoside Analogues
Organic letters. 2021 Nov. 03, v. 23, no. 22
2021
Abstract: Novel C-4′,C-5′ cyclobutane-fused spirocyclic ribonucleoside analogues were prepared. Thermal [2 + 2] cycloaddition between dichloroketene and readily derived 4′-exo-methylene furanoses afforded a first entry to the required constrained ribofuranoses, ... ...
| Abstract | Novel C-4′,C-5′ cyclobutane-fused spirocyclic ribonucleoside analogues were prepared. Thermal [2 + 2] cycloaddition between dichloroketene and readily derived 4′-exo-methylene furanoses afforded a first entry to the required constrained ribofuranoses, relying on a carbonyl transposition sequence. Alternatively, an unusual stereoselective ionic [2 + 2] cycloaddition using methyl propiolate promoted by methylaluminoxane gave a complementary, more direct approach to such ribofuranoses. Further conversion to the constrained adenosine analogues revealed promising structure-dependent inhibition of the protein methyltransferase PRMT5:MEP50 complex in the (sub)micromolar range. |
|---|---|
| Keywords | adenosine ; cycloaddition reactions ; methyltransferases ; stereoselective synthesis ; stereoselectivity |
| Language | English |
| Dates of publication | 2021-1103 |
| Size | p. 8828-8833. |
| Publishing place | American Chemical Society |
| Document type | Article |
| ISSN | 1523-7052 |
| DOI | 10.1021/acs.orglett.1c03334 |
| Database | NAL-Catalogue (AGRICOLA) |
More links
Kategorien
Order via subito
This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.
Inter-library loan at ZB MED
Your chosen title can be delivered directly to ZB MED Cologne location if you are registered as a user at ZB MED Cologne.