Synthesis of functionally diverse and conformationally constrained polycyclic analogues of proline and prolinol.
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 pendant groups on the original proline motif as well as on the aromatic moiety.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
Papeo
Gianluca
G
Angiolini
Mauro
M
Fettis
Kamal
K
Beretta
Marco
M
Munro
Alexander
A
D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*
D006575:Heterocyclic Compounds, 3-Ring; D011759:Pyrrolidines; C010509:prolinol; D011392:Proline