Tetrahedron

β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids

HH Wasserman, H Matsuyama, RP Robinson

文献索引：Wasserman, Harry H; Matsuyama, Haruo; Robinson, Ralph P Tetrahedron, 2002 , vol. 58, # 35 p. 7177 - 7190

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被引用次数: 51

摘要

Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)- dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed:(1) transamidation of N-(aminoalkyl) lactams,(2) β- lactam-lactim ether condensation followed by reductive cleavage of the bicyclic 4- ...