Synthesis of functionally diverse and conformationally constrained polycyclic analogues of proline and prolinol

…, G Papeo, M Angiolini, K Fettis, M Beretta…

Index: Hanessian, Stephen; Papeo, Gianluca; Angiolini, Mauro; Fettis, Kamal; Beretta, Marco; Munro, Alexander Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7204 - 7218

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Citation Number: 29

Abstract

Alkylation of the monoenolate of N-Boc-l-pyroglutamic acid methyl ester with a variety of benzylic halides and their homologues gave the corresponding anti-C-4-alkylated products as major products. Formation of the N-Boc-iminium ion and Friedel-Crafts intramolecular cationic ring closure afforded a series of fused 1-azacyclodihydroindene derivatives with interesting topologies. Functional diversity was introduced via further manipulation of ...