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Synthesis 2004(6): 840-846  
DOI: 10.1055/s-2004-816001
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© Georg Thieme Verlag Stuttgart · New York

New Synthesis and Application of 3-Substituted Prolinols

Meng-Yang Chang*a, Chung-Yi Chenb, Min-Ruey Tasib, Tze-Wei Tsengb, Nein-Chen Chang*b
a Department of Applied Chemistry, National University of Kaohsiung, Kaohsiung 811, Taiwan
b Department of Chemistry, National Sun Yat-Sen University, Kaohsiung 804, Taiwan
Fax: +886(7)5919348; e-Mail: mychang@nuk.edu.tw;
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Publication History

Received 11 December 2003
Publication Date:
04 March 2004 (online)

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Abstract

Carbon skeleton of polysubstituted pyroglutamates with three contiguous asymmetric centers was built up in one base-induced coupling/cyclization reaction of α-sulfonylacetamide with 2-bromo-2-propenoates. A simple transformation to 3-substituted prolinols can be easily achieved via reduction and desulfonation. A ring expansion of prolinol has been used as the key step in the formal synthesis of isoguvacine and paroxetine. The one-pot conversion of 3-substituted prolinol to the 3-substituted pyroglutamic acid is also reported.

Keywords

glutarimides - stepwise [3+2] annulation - pyroglutamates - prolinol - isoguvacine - paroxetine