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Synthetic Studies of Polysubstituted Pyroglutamates and Its Applications in Natural Products Synthesis

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.

Identiferoai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0703103-095535
Date03 July 2003
CreatorsSun, Pei-Pei
ContributorsTeng-Yuan Dong, Yung-Son Hon, Chin-Hsing Chou, Chi-Wi Ong, Cherng-Chyi Tzeng, Nein-Chen Chang
PublisherNSYSU
Source SetsNSYSU Electronic Thesis and Dissertation Archive
LanguageCholon
Detected LanguageEnglish
Typetext
Formatapplication/pdf
Sourcehttp://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0703103-095535
Rightswithheld, Copyright information available at source archive

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