Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid

被引:33
作者
Higashibayashi, S [1 ]
Kohno, M [1 ]
Goto, T [1 ]
Suziki, K [1 ]
Mori, T [1 ]
Hashimoto, K [1 ]
Nakata, M [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
thiostrepton; thiazolines; thioamides; sulfinimines; dihydroxyisoleucine;
D O I
10.1016/j.tetlet.2004.03.099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dihydroxyisoleucine-, thiazoline- and dehydroamino acid-containing pentapeptide of the thiostrepton family of peptide antibiotics was synthesized, which featured the beta-lactone opening by phenylselenylation, the vinylzinc addition to the chiral sulfinimine, the Wipf oxazoline-thiazoline conversion method and the oxidative syn-elimination of the phenylseleno group. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:3707 / 3712
页数:6
相关论文
共 65 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]  
Asensio A, 2001, EUR J ORG CHEM, V2001, P1449
[3]   THIOSTREPTON - DEGRADATION PRODUCTS + STRUCTURAL FEATURES [J].
BODANSZKY, M ;
BIRKHIMER, CA ;
FRIED, J ;
ALICINO, J ;
WILLIAMS, NJ ;
KEELER, BT ;
COHEN, AI ;
SHEEHAN, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (12) :2478-&
[4]   THE SYNTHESIS OF OPTICALLY-ACTIVE THIAZOLINE AND THIAZOLE DERIVED PEPTIDES FROM N-PROTECTED ALPHA-AMINO-ACIDS [J].
BODEN, CDJ ;
PATTENDEN, G ;
YE, T .
SYNLETT, 1995, (05) :417-419
[5]   Stereospecific synthesis of 2,3-disubstituted aziridines from β-alkylamino phenylselenides [J].
Boivin, S ;
Outurquin, F ;
Paulmier, C .
TETRAHEDRON LETTERS, 2000, 41 (05) :663-666
[6]   Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids [J].
Bravo, P ;
Crucianelli, M ;
Vergani, B ;
Zanda, M .
TETRAHEDRON LETTERS, 1998, 39 (42) :7771-7774
[7]   THE ACTION OF DIETHYLAMINOSULFUR TRIFLUORIDE (DAST) ON TRANS-4-AMIDO-3-CHROMANOLS - PREPARATION OF CIS-AMIDOALCOHOLS VIA OXAZOLINES [J].
BURRELL, G ;
EVANS, JM ;
JONES, GE ;
STEMP, G .
TETRAHEDRON LETTERS, 1990, 31 (25) :3649-3652
[8]   Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].
Cogan, DA ;
Liu, GC ;
Kim, KJ ;
Backes, BJ ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019
[9]   Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].
Cogan, DA ;
Liu, GC ;
Ellman, J .
TETRAHEDRON, 1999, 55 (29) :8883-8904
[10]   PYBOP - A NEW PEPTIDE COUPLING REAGENT DEVOID OF TOXIC BY-PRODUCT [J].
COSTE, J ;
LENGUYEN, D ;
CASTRO, B .
TETRAHEDRON LETTERS, 1990, 31 (02) :205-208