Metal-Templated Macrolactamization of Triamino and Tetramino Esters. Facile Synthesis of Macrocyclic Spermidine and Spermine Alkaloids,(S)-(+)- …

…, K Ishihara, N Hanaki, S Ohara, H Yamamoto

Index: Kuroki, Yoshichika; Ishihara, Kazuaki; Hanaki, Naoyuki; Ohara, Suguru; Yamamoto, Hisashi Bulletin of the Chemical Society of Japan, 1998 , vol. 71, # 5 p. 1221 - 1230

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Citation Number: 39

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.