Solid phase heterocyclic chemistry

被引:249
作者
Krchnak, V [1 ]
Holladay, MW [1 ]
机构
[1] ChemRx Adv Technol Inc, Tucson, AZ 85747 USA
关键词
D O I
10.1021/cr010123h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A review is given of the methods for the traceless solid-phase synthesis of various heterocyclic compounds, whereby the presence of obvious traces of linkage to the solid support are eliminated. These approaches are organized into several distinct categories as follows: i) use of C-H linkers results in formation of a C-H bond in the seceding molecule during the cleavage step, ii) use of N-H linkers results in formation of an N-H bond in seceding molecule, iii) application of a cyclative cleavage strategy yields a newly formed C-N bond, and iiii) inducement of modifications to the target molecule during or after the cleavage step obscures or obliterates the previous point of attachment to the solid support.
引用
收藏
页码:61 / 91
页数:31
相关论文
共 153 条
[51]  
Gmeiner P, 1996, SYNTHESIS-STUTTGART, P1196
[52]   Solid supported high-throughput organic synthesis of peptide β-turn mimetics via Petasis reaction/diketopiperazine formation [J].
Golebiowski, A ;
Klopfenstein, SR ;
Chen, JJ ;
Shao, X .
TETRAHEDRON LETTERS, 2000, 41 (25) :4841-4844
[53]   REDUCTIVE ALKYLATION ON A SOLID-PHASE - SYNTHESIS OF A PIPERAZINEDIONE COMBINATORIAL LIBRARY [J].
GORDON, DW ;
STEELE, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (01) :47-50
[54]   Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones [J].
Gouilleux, L ;
Fehrentz, JA ;
Winternitz, F ;
Martinez, J .
TETRAHEDRON LETTERS, 1996, 37 (39) :7031-7034
[55]   ''Traceless'' solid-phase synthesis of furans via 1,3-dipolar cycloaddition reactions of isomunchnones [J].
Gowravaram, MR ;
Gallop, MA .
TETRAHEDRON LETTERS, 1997, 38 (40) :6973-6976
[56]   Solid-phase synthesis of C-terminal peptide aldehydes from amino acetals anchored to a backbone amide linker (BAL) handle [J].
Guillaumie, F ;
Kappel, JC ;
Kelly, NM ;
Barany, G ;
Jensen, KJ .
TETRAHEDRON LETTERS, 2000, 41 (32) :6131-6135
[57]   Linkers and cleavage strategies in solid-phase organic synthesis and combinatorial chemistry [J].
Guillier, F ;
Orain, D ;
Bradley, M .
CHEMICAL REVIEWS, 2000, 100 (06) :2091-2157
[58]   Alkylidenation of esters on solid support and traceless synthesis of 2-substituted benzofurans [J].
Guthrie, EJ ;
Macritchie, J ;
Hartley, RC .
TETRAHEDRON LETTERS, 2000, 41 (25) :4987-4990
[59]   Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin [J].
Hamper, BC ;
Gan, KZ ;
Owen, TJ .
TETRAHEDRON LETTERS, 1999, 40 (27) :4973-4976
[60]   Solid-phase synthesis of acyclic and cyclic amino acid derived urea peptidomimetics using phoxime resin [J].
Hamuro, Y ;
Marshall, WJ ;
Scialdone, MA .
JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (02) :163-172