Progress toward the total synthesis of callipeltin A (I):: Asymmetric synthesis of (3S,4R)-3,4-dimethylglutamine

被引:55
作者
Liang, B [1 ]
Carroll, PJ [1 ]
Joullié, MM [1 ]
机构
[1] Univ Penn, Dept Chem, Xray Crystallog Facil, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol006679t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] During the total synthesis of the novel cyclic depsipeptide callipeltin A (1), the unit (3S,4R)-3,4-dimethylglutamine, was successfully synthesized by asymmetric Michael addition and subsequent electrophilic azidation. The key feature of this approach is the generation of three adjacent stereogenic centers using the same camphorsultam chiral auxiliary.
引用
收藏
页码:4157 / 4160
页数:4
相关论文
共 29 条
[1]   ASYMMETRIC MICHAEL-ADDITIONS - PRACTICALLY COMPLETELY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINE FROM CYCLOHEXANONE AND PROLINYL METHYL-ETHER BY OMEGA-NITROSTYRENES TO GIVE U- 2-(1'-ARYL-2'-NITROETHYL)CYCLOHEXANONES [J].
BLARER, SJ ;
SCHWEIZER, WB ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1982, 65 (05) :1637-1654
[2]   FROM CRYSTAL STATICS TO CHEMICAL-DYNAMICS [J].
BURGI, HB ;
DUNITZ, JD .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (05) :153-161
[3]   GEOMETRICAL REACTION COORDINATES .2. NUCLEOPHILIC ADDITION TO A CARBONYL GROUP [J].
BURGI, HB ;
DUNITZ, JD ;
SHEFTER, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (15) :5065-5067
[4]   A 2-STEP SYNTHESIS OF CAMPHOSULTAM [J].
CAPET, M ;
DAVID, F ;
BERTIN, L ;
HARDY, JC .
SYNTHETIC COMMUNICATIONS, 1995, 25 (21) :3323-3327
[5]  
DAuria MV, 1996, TETRAHEDRON, V52, P9589
[6]   STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES - A NEW APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-HYDRAZINO AND ALPHA-AMINO-ACID DERIVATIVES [J].
EVANS, DA ;
BRITTON, TC ;
DOROW, RL ;
DELLARIA, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6395-6397
[7]   A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF VANCOMYCIN-RELATED ARYLGLYCINES BY ENOLATE AZIDATION [J].
EVANS, DA ;
EVRARD, DA ;
RYCHNOVSKY, SD ;
FRUH, T ;
WHITTINGHAM, WG ;
DEVRIES, KM .
TETRAHEDRON LETTERS, 1992, 33 (09) :1189-1192
[8]   THE TOTAL SYNTHESES OF THE ISODITYROSINE-DERIVED CYCLIC TRIPEPTIDES OF4949-III AND K-13 - DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF K-13 [J].
EVANS, DA ;
ELLMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1063-1072
[9]   THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO AND ALPHA-HYDRAZINO ACID-DERIVATIVES VIA THE STEREOSELECTIVE AMINATION OF CHIRAL ENOLATES WITH AZODICARBOXYLATE ESTERS [J].
EVANS, DA ;
BRITTON, TC ;
DOROW, RL ;
DELLARIA, JF .
TETRAHEDRON, 1988, 44 (17) :5525-5540
[10]   ELECTROPHILIC AZIDE TRANSFER TO CHIRAL ENOLATES - A GENERAL-APPROACH TO THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
EVANS, DA ;
BRITTON, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) :6881-6883