Solid phase synthesis of fumitremorgin, verruculogen and tryprostatin analogs based on a cyclization/cleavage strategy

被引:60
作者
van Loevezijn, A
van Maarseveen, JH
Stegman, K
Visser, GM
Koomen, GJ
机构
[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands
[2] Solvay Pharmaceut Res Labs, NL-1380 DA Weesp, Netherlands
关键词
solid-phase synthesis; Pictet-Spengler reactions; amino acids and derivatives; coupling reagents;
D O I
10.1016/S0040-4039(98)00931-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A solid phase synthesis towards structural analogs of fumitremorgins, verruculogens and tryprostatins using a cyclization/cleavage strategy was developed. To prove the general applicability of the route, a representative set of 42 single compounds (as diastereomeric mixtures) was prepared by parallel synthesis and analyzed with LC/MS. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4737 / 4740
页数:4
相关论文
共 21 条
[1]   EFFICIENT COUPLING OF ALPHA,ALPHA-DIMETHYL AMINO-ACID USING A NEW CHLORO IMIDAZOLIDIUM REAGENT, CIP [J].
AKAJI, K ;
KURIYAMA, N ;
KISO, Y .
TETRAHEDRON LETTERS, 1994, 35 (20) :3315-3318
[2]   TETRAMETHYLFLUOROFORMAMIDINIUM HEXAFLUOROPHOSPHATE - A RAPID-ACTING PEPTIDE COUPLING REAGENT FOR SOLUTION AND SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5401-5402
[3]   ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].
CARPINO, LA ;
COHEN, BJ ;
STEPHENS, KE ;
SADATAALAEE, SY ;
TIEN, JH ;
LANGRIDGE, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734
[4]   ADVANTAGEOUS APPLICATIONS OF AZABENZOTRIAZOLE (TRIAZOLOPYRIDINE)-BASED COUPLING REAGENTS TO SOLID-PHASE PEPTIDE-SYNTHESIS [J].
CARPINO, LA ;
EL-FAHAM, A ;
MINOR, CA ;
ALBERICIO, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (02) :201-203
[5]   1-HYDROXY-7-AZABENZOTRIAZOLE - AN EFFICIENT PEPTIDE COUPLING ADDITIVE [J].
CARPINO, LA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4397-4398
[6]   TREMORGENIC TOXIN FROM PENICILLIUM-VERRUCULOSUM [J].
COLE, RJ ;
DAVIS, ND ;
BLANKENSHIP, BR ;
DIENER, UL ;
MOORE, JH ;
KIRKSEY, JW .
APPLIED MICROBIOLOGY, 1972, 24 (02) :248-+
[7]   COUPLING N-METHYLATED AMINO-ACIDS USING PYBROP AND PYCLOP HALOGENOPHOSPHONIUM SALTS - MECHANISM AND FIELDS OF APPLICATION [J].
COSTE, J ;
FREROT, E ;
JOUIN, P .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2437-2446
[8]   Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
TETRAHEDRON, 1997, 53 (01) :59-72
[9]   Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .1. Taxonomy, fermentation, isolation and biological properties [J].
Cui, CB ;
Kakeya, H ;
Okada, G ;
Onose, R ;
Osada, H .
JOURNAL OF ANTIBIOTICS, 1996, 49 (06) :527-533
[10]   DIVERSOMERS - AN APPROACH TO NONPEPTIDE, NONOLIGOMERIC CHEMICAL DIVERSITY [J].
DEWITT, SH ;
KIELY, JS ;
STANKOVIC, CJ ;
SCHROEDER, MC ;
CODY, DMR ;
PAVIA, MR .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1993, 90 (15) :6909-6913