APPLICATION OF REMOTE PHOTOCYCLIZATION WITH A PAIR SYSTEM OF PHTHALIMIDE AND METHYLTHIO GROUPS - A PHOTOCHEMICAL-SYNTHESIS OF CYCLIC PEPTIDE MODELS

被引:17
作者
SATO, Y [1 ]
NAKAI, H [1 ]
WADA, M [1 ]
MIZOGUCHI, T [1 ]
HATANAKA, Y [1 ]
KANAOKA, Y [1 ]
机构
[1] HOKKAIDO UNIV, FAC PHARMACEUT SCI, KITA KU, SAPPORO, HOKKAIDO 060, JAPAN
关键词
PHOTOCHEMISTRY; REGIOSELECTIVE REMOTE PHOTOCYCLIZATION; SULFIDE-CONTAINING PHTHALIMIDE; DONOR ACCEPTOR PAIR SYSTEM; MACROCYCLIC SYNTHESIS; CYCLIC PEPTIDE MODEL;
D O I
10.1248/cpb.40.3174
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Application of regioselective remote photocyclization of a pair system consisting of a phthalimide group and a methylthio group to a homologous series of N-substituted phthalimides (4 and 5) possessing a terminal sulfide function in the amide side chain was investigated. On irradiation, medium to large membered cyclic peptide-like compunds (6, 7 and 9), up to a thirty-eight membered ring product (6f), were synthesized in moderate yields.
引用
收藏
页码:3174 / 3180
页数:7
相关论文
共 46 条
[1]   AMINO ACIDS .5. PHTHALYL DERIVATIVES [J].
BILLMAN, JH ;
HARTING, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (04) :1473-1474
[2]   PEPTIDE ANTIBIOTICS [J].
BODANSZKY, M ;
PERLMAN, D .
SCIENCE, 1969, 163 (3865) :352-+
[3]  
BOTTCHER KA, 1913, CHEM BER, V46, P3158
[4]   PREPARATION OF DERIVATIVES AND ANALOGS OF THE MACROCYCLIC OLIGOMERS OF ETHYLENE-OXIDE (CROWN COMPOUNDS) [J].
BRADSHAW, JS ;
STOTT, PE .
TETRAHEDRON, 1980, 36 (04) :461-510
[5]   CENTENARY LECTURE - BIOMIMETIC CHEMISTRY [J].
BRESLOW, R .
CHEMICAL SOCIETY REVIEWS, 1972, 1 (04) :553-580
[6]   DESIGN OF COMPLEXES BETWEEN SYNTHETIC HOSTS AND ORGANIC GUESTS [J].
CRAM, DJ ;
CRAM, JM .
ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (01) :8-14
[7]   HOST-GUEST CHEMISTRY [J].
CRAM, DJ ;
CRAM, JM .
SCIENCE, 1974, 183 (4127) :803-809
[8]   WHY CYCLIC PEPTIDES - COMPLEMENTARY APPROACHES TO CONFORMATIONS [J].
DEBER, CM ;
MADISON, V ;
BLOUT, ER .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (03) :106-113
[9]  
DUGAS H, 1981, BIOORG CHEM, P255
[10]  
GABRIEL S, 1908, CHEM BER, V41, P2014