We have explored a formal [3+2] strategy that is synthetically useful for constructing polysubstituted pyroglutamates with three contiguous chiral centers in one step. Base-induced coupling/cyclization reactions of a-sulfonylacetamide with various ethyl (Z)-2-bromo-2-propenoates have been carried out. This reaction with high diastereoselectivity has been applied to the synthesis of Rolipram, Chlorpheg, Baclofen, Pseudoheliotridane and Kainic acid.
| Identifer | oai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0703103-095535 |
| Date | 03 July 2003 |
| Creators | Sun, Pei-Pei |
| Contributors | Teng-Yuan Dong, Yung-Son Hon, Chin-Hsing Chou, Chi-Wi Ong, Cherng-Chyi Tzeng, Nein-Chen Chang |
| Publisher | NSYSU |
| Source Sets | NSYSU Electronic Thesis and Dissertation Archive |
| Language | Cholon |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0703103-095535 |
| Rights | withheld, Copyright information available at source archive |
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