A versatile approach to the activated form of (3S, 4R)-statine and its analogues

被引:13
作者
Huang, PQ [1 ]
Ye, JL
Chen, Z
Ruan, YP
Gao, JX
机构
[1] Xiamen Univ, Dept Chem, Xiamen 361005, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1080/00397919808005095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise and versatile approach to the activated form of(3S, 4R)-statine 6 and its analogues is described. The key steps involve reductive alkylation of (S)-O-tert-butyldimethysilylmalimide 12.
引用
收藏
页码:417 / 426
页数:10
相关论文
共 23 条
[1]   ASYMMETRIC-SYNTHESIS VIA ACETAL TEMPLATES .14. PREPARATION OF ENANTIOMERICALLY PURE (3S,4S)-STATINE AND (3S,4R)-STATINE DERIVATIVES [J].
ANDREW, RG ;
CONROW, RE ;
ELLIOTT, JD ;
JOHNSON, WS ;
RAMEZANI, S .
TETRAHEDRON LETTERS, 1987, 28 (52) :6535-6538
[2]   TOTAL SYNTHESIS OF BLEOMYCIN-A(2) AND RELATED AGENTS .1. SYNTHESIS AND DNA-BINDING PROPERTIES OF THE EXTENDED C-TERMINUS - TRIPEPTIDE-S, TETRAPEPTIDE-S, PENTAPEPTIDE-S, AND RELATED AGENTS [J].
BOGER, DL ;
COLLETTI, SL ;
HONDA, T ;
MENEZES, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5607-5618
[3]   A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].
BURGESS, LE ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662
[4]   Ready access to stereodefined beta-hydroxy-gamma-amino acids. Enantioselective synthesis of fully protected cyclohexylstatine. [J].
Castejon, P ;
Moyano, A ;
Pericas, MA ;
Riera, A .
TETRAHEDRON, 1996, 52 (20) :7063-7086
[5]  
CASTEJON P, 1996, CHEMEUR J, V2, P8
[6]  
DAVE HR, 1967, J CHEM SOC CHEM COMM, P743
[7]   SYNTHESIS AND REDUCTION OF ALPHA-AMINO KETONES DERIVED FROM LEUCINE [J].
DUFOUR, MN ;
JOUIN, P ;
PONCET, J ;
PANTALONI, A ;
CASTRO, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (11) :1895-1899
[8]   A STEREOSELECTIVE SYNTHESIS OF (+/-)-H12-HISTRIONICOTOXIN AND RELATED PHOTOAFFINITY-LABELED CONGENERS [J].
EVANS, DA ;
THOMAS, EW ;
CHERPECK, RE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) :3695-3700
[9]  
GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991
[10]   REAGENT CONTROL IN THE ALDOL ADDITION-REACTION OF CHIRAL BORON ENOLATES WITH CHIRAL ALPHA-AMINO ALDEHYDES - TOTAL SYNTHESIS OF (3S,4S)-STATINE [J].
GENNARI, C ;
PAIN, G ;
MORESCA, D .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6248-6249