Tetrahedron

Fused and bridged bi-and tri-cyclic lactams via sequential metallo-azomethine ylide cycloaddition–lactamisation

P Blaney, R Grigg, Z Rankovic, M Thornton-Pett, J Xu

Index: Blaney, Paul; Grigg, Ronald; Rankovic, Zoran; Thornton-Pett, Mark; Xu, Juan Tetrahedron, 2002 , vol. 58, # 9 p. 1719 - 1737

Full Text: HTML

Citation Number: 32

Abstract

Aldimines of α-amino esters derived from aldehydes bearing an α-, β-or γ-protected amino group undergo AgOAc/R3N catalysed cycloaddition to electronegative olefins (dipolarophile). Subsequent unmasking of the amino group and lactamisation, spontaneous in most cases, generates 5–7 membered fused and bridged bi-and tri-cyclic lactams. The regioselectivity of the lactamisation is controlled by appropriate choice of the dipolarophile.

Related Articles:

Evaluation of chelating agents as anti-angiogenic therapy through copper chelation

[Camphausen, Kevin; Sproull, Mary; Tantama, Steve; Venditto, Vincent; Sankineni, Sandeep; Scott, Tamalee; Brechbiel, Martin W. Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 19 p. 5133 - 5140]

Studies on the total synthesis of bouvardin and deoxybouvardin: cyclic hexapeptide cyclization studies and preparation of key partial structures

[Journal of Organic Chemistry, , vol. 53, # 3 p. 487 - 499]

Studies on the total synthesis of bouvardin and deoxybouvardin: cyclic hexapeptide cyclization studies and preparation of key partial structures

[Journal of Organic Chemistry, , vol. 53, # 3 p. 487 - 499]

Camptothecin-20-PEG ester transport forms: the effect of spacer groups on antitumor activity

[Bioorganic and Medicinal Chemistry, , vol. 6, # 5 p. 551 - 562]

Verbesserte Synthese von tert.??Butyloxycarbonyl??aminosäuren durch pH??Stat??Reaktion

[Justus Liebigs Annalen der Chemie, , vol. 702, p. 188 - 196]

More Articles...