Glycal Ethers as Starting Materials in C-Nucleoside Synthesis |
| |
| Authors: | Andrew Kaye Colin B. Reese Stephen Neidle |
| |
| Affiliation: | 1. Department of Chemistry , King's College London , Strand, London, WC2R 2LS, England;2. Institute of Cancer Research , Clifton Avenue, Sutton, Surrey, SM2 5PX |
| |
| Abstract: | Abstract When 3,4,6-tri-O-benzyl-g-glucal (3) is treated with thallium (III) nitrate, trihydrate in acetonitrile, 2,5-anhydro-3,4,6-tri-O-benzyl-D-mannose (4), a precursor of the showdomycin analogue (5), is obtained. Ring-contraction of (3) can also be effected by a three-step process [(i) PhSeCl, tetrahydrofuran, (ii) Et3N, H2O; (iii) 3-ClC6-H4CO3H, KeOH]. Other examples of these ring-contraction reactions are described. |
| |
| Keywords: | |
|
|
