174320-11-7Relevant articles and documents
Lithium and proton templated ω-polyazamacrolactamization, new general routes to macrocyclic polyamines
Drandarov, Konstantin,Hesse, Manfred
, p. 7213 - 7216 (2007/10/03)
A general, lithium templated/catalyzed ω-polyazamacrolactamization method for the synthesis of macrocyclic polyamines including spermidine and spermine alkaloids is presented. The formation of 12-, 13-, 16-, 17-, and 19-membered N3, N4, N5, and N6 containing rings is described. A proton templated/catalyzed macrolactamization of some ω-polyazaaminoesters is also observed.
Metal-Templated Macrolactamization of Triamino and Tetramino Esters. Facile Synthesis of Macrocyclic Spermidine and Spermine Alkaloids, (S)-(+)-Dihydroperiphylline, (±)-Buchnerine, (±)-Verbacine, (±)-Verbaskine, and (±)-Verbascenine
Kuroki, Yoshichika,Ishihara, Kazuaki,Hanaki, Naoyuki,Ohara, Suguru,Yamamoto, Hisashi
, p. 1221 - 1230 (2007/10/03)
The total synthesis of spermidine and spermine alkaloids. (S)-(+)-dihydroperiphylline (1), (±)-buchnerine (2), (±)-verbacine (3), (±)-verbaskine (4), and (±)-verbascenine (5), is described. The construction of macrocyclic lactams has been efficiently accomplished by the metal-templated cyclization of triamino esters and tetraamino esters. It was also found that the antimony(III) ethoxide is useful as an intermolecular amidation catalyst.