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Metal-Templated Macrolactamization of Triamino and Tetramino Esters. Facile Synthesis of Macrocyclic Spermidine and Spermine Alkaloids, ( S )-(+)-Dihydroperiphylline, (±)-Buchnerine, (±)-Verbacine, (±)-Verbaskine, and (±)-Verbascenine

1998; Oxford University Press; Volume: 71; Issue: 5 Linguagem: Inglês

10.1246/bcsj.71.1221

1348-0634

Yoshichika Kuroki, Kazuaki Ishihara, Naoyuki Hanaki, Suguru Ohara, Hisashi Yamamoto,

Synthetic Organic Chemistry Methods

Abstract 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.