USE OF DIKETOPIPERAZINES FOR DETERMINING ABSOLUTE CONFIGURATIONS OF α-SUBSTITUTED SERINES BY 1H-NMR SPECTROSCOPY

被引：12

作者：

Sano, Shigeki ^{[1
]}

Nakao, Michiyasu ^{[1
]}

Takeyasu, Masanori ^{[1
]}

Kitaike, Syuji ^{[1
]}

Yoshioka, Yasuko ^{[1
]}

Nagao, Yoshimitsu ^{[1
]}

机构：

[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Sho, Tokushima, Japan

来源：

HETEROCYCLES | 2009年 / 79卷

关键词：

Diketopiperazine; Absolute Configuration; alpha-Substituted Serine; H-1-NMR Analysis; DKP Method; ASYMMETRIC TOTAL-SYNTHESIS; ALDOL-TYPE REACTION; O-METHYLMANDELATE; SPHINGOFUNGIN-E; MYRIOCIN; (+)-LACTACYSTIN; EFFICIENT; THERMOZYMOCIDIN; (+)-CONAGENIN; REARRANGEMENT;

D O I：

10.3987/COM-08-S(D)47

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral alpha-substituted serine of interest was transformed into both of the corresponding diastereomers of diketopiperazines utilizing L- and D-phenylalanine methyl ester hydrochloride. The absolute configuration of the original chiral alpha-substituted serine was determined by H-1-NMR analyses of the resulting diastereomers.

引用

收藏

页码：781 / 789

页数：9

相关论文

共 50 条

[1] α,β-unsaturated β-silyl imide substrates for catalytic, enantioselective conjugate additions:: A total synthesis of (+)-lactacystin and the discovery of a new proteasome inhibitor [J].

Balskus, Emily P. ;

Jacobsen, Eric N. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6810-6812

[2] 2-BENZOYLAMINO-2-DEOXY-2-HYDROXYMETHYL-D-HEXONO-1,4-LACTONES - SYNTHESIS FROM D-FRUCTOSE AND UTILIZATION IN THE TOTAL SYNTHESIS OF THERMOZYMOCIDIN (MYRIOCIN) [J].

BANFI, L ;

BERETTA, MG ;

COLOMBO, L ;

GENNARI, C ;

SCOLASTICO, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (08) :1613-1619

[3] Investigation of diketopiperazines containing a guanidino-functionalized sidechain as potential catalysts of enantioselective Strecker reactions [J].

Becker, C ;

Hoben, C ;

Schollmeyer, D ;

Scherr, G ;

Kunz, H .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) :1497-1499

[4] Total synthesis of (+)-conagenin [J].

Chakraborty, Tushar Kanti ;

Sudhakar, Gangarajula .

TETRAHEDRON LETTERS, 2006, 47 (33) :5847-5849

[5] TOTAL SYNTHESIS OF (+)-LACTACYSTIN FROM D-GLUCOSE [J].

CHIDA, N ;

TAKEOKA, J ;

TSUTSUMI, N ;

OGAWA, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (07) :793-794

[6] Determination of the absolute configuration of amines and alpha-amino acids by H-1 NMR of (R)-O-aryllactic acid amides [J].

Chinchilla, R ;

Falvello, LR ;

Najera, C .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7285-7290

[7]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1676, DOI 10.1002/(SICI)1521-3773(19980703)37:12<1676::AID-ANIE1676>3.0.CO

[8]

2-T

[9] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[10] SYNTHESIS OF ALPHA-AZIDO ALDEHYDES - STEREOSELECTIVE FORMAL ACCESS TO THE IMMUNOSUPPRESSANT MYRIOCIN [J].

DELOISY, S ;

THANG, TT ;

OLESKER, A ;

LUKACS, G .

TETRAHEDRON LETTERS, 1994, 35 (27) :4783-4786

← 1 2 3 4 5 →