β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids
HH Wasserman, H Matsuyama, RP Robinson
Index: Wasserman, Harry H; Matsuyama, Haruo; Robinson, Ralph P Tetrahedron, 2002 , vol. 58, # 35 p. 7177 - 7190
Full Text: HTML
Citation Number: 51
Abstract
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- ...
Related Articles:
Reactivity of β-Lactamido N-Sulfonyl Radicals
[Begley, Michael J.; Crombie, Leslie; Haigh, David; Jones, Raymond C. F.; Osborne, Steven; Webster, Richard A. B. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993 , # 17 p. 2027 - 2046]
Medium ring heterocycles: transamidation reactions of β-lactams
[Crombie, Leslie; Jones, Raymond C. F.; Osborne, Steven; Mat-Zin, Ab. Rasid Journal of the Chemical Society, Chemical Communications, 1983 , # 17 p. 959 - 960]
Reactivity of β-Lactamido N-Sulfonyl Radicals
[Begley, Michael J.; Crombie, Leslie; Haigh, David; Jones, Raymond C. F.; Osborne, Steven; Webster, Richard A. B. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993 , # 17 p. 2027 - 2046]