β-Lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids
作者： Harry H Wasserman , Haruo Matsuyama , Ralph P Robinson
DOI: 10.1016/S0040-4020(02)00731-7
关键词:
摘要: Abstract Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine ( 1 ) and (±)-dihydroperiphylline 2 as well related spermine alkaloid (±)-verbascenine 3 were accomplished by means sequential ring expansions smaller lactam rings. Three expansion methods employed: (1) transamidation N -(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed reductive cleavage bicyclic 4-oxotetrahydropyrimidine product with NaBH CN/AcOH (3) acyl hydrazine formation N–N bond Na/NH . Each synthesis features a 4-phenylazetidin-2-one intermediate that undergoes transamidative or lactim condensation.
elsevier.com
sci-hub.se 参考文章(47)
Uriel Bachrach, Function of naturally occurring polyamines ,(1973)
Harry H. Wasserman, Gregory D. Berger, The use of β-lactams in the synthesis of spermine and spermidine alkaloids Tetrahedron. ,vol. 39, pp. 2459- 2464 ,(1983) , 10.1016/S0040-4020(01)92138-6
R. Hocquemiller, A. Cavé, H.-P. Husson, Alcaloides du peripterygia marginata (baill.) lues. (célastracées)—I Tetrahedron. ,vol. 33, pp. 645- 651 ,(1977) , 10.1016/0040-4020(77)80304-9
HIROKI TAKAHATA, AKIRA TOMOGUCHI, TAKAO YAMAZAKI, The Chemistry of Lactim Ethers. V. Reaction of Lactim Thioethers with β-Aminoesters Chemical & Pharmaceutical Bulletin. ,vol. 29, pp. 2526- 2530 ,(1981) , 10.1248/CPB.29.2526
Nobuhiro Itoh, Haruo Matsuyama, Masato Yoshida, Nobumasa Kamigata, Masahiko Iyoda, Asymmetric synthesis of 4-phenyl-1,5-diazacyclooctan-2-one using optically active vinyl sulfoxides Bulletin of the Chemical Society of Japan. ,vol. 68, pp. 3121- 3130 ,(1995) , 10.1246/BCSJ.68.3121
Jack E. Baldwin, John Cutting, William Dupont, Lawrence Kruse, Lee Silberman, Richard C. Thomas, 5-Endo-trigonal reactions: a disfavoured ring closure Journal of the Chemical Society, Chemical Communications. pp. 736- 738 ,(1976) , 10.1039/C39760000736
Harry D. Wasserman, Michael R. Leadbetter, Ihor E. Kopka, A total synthesis of (±)-dihydropalustrine Tetrahedron Letters. ,vol. 25, pp. 2391- 2394 ,(1984) , 10.1016/S0040-4039(01)80263-X
Melvin Fields, Doris E. Walz, Seymour Rothchild, The Synthesis of Ethyl Acetamidocyanoacetate, DL-Lysine, DL-Ornithine and DL-Tyrosine Labeled with Isotopic Carbon1 Journal of the American Chemical Society. ,vol. 73, pp. 1000- 1002 ,(1951) , 10.1021/JA01147A034
Harry H. Wasserman, Rudolf K. Brunner, John D. Buynak, Charles G. Carter, Teruo Oku, Ralph P. Robinson, Total synthesis of (.+-.)-O-methylorantine Journal of the American Chemical Society. ,vol. 107, pp. 519- 521 ,(1985) , 10.1021/JA00288A050
Jiangao Song, Manfred Hesse, Synthesis of (±)tetrahydromyricoidine Tetrahedron. ,vol. 49, pp. 6797- 6804 ,(1993) , 10.1016/S0040-4020(01)80423-3