TOTAL SYNTHESIS OF (+) MONOMORINE-I FROM CHIRAL CYCLIC BETA-ENAMINO ESTER

被引：58

作者：

SALIOU, C ^{[1
]}

FLEURANT, A ^{[1
]}

CELERIER, JP ^{[1
]}

LHOMMET, G ^{[1
]}

机构：

[1] UNIV PARIS 06, CHIM HETEROCYCLES LAB, CNRS, 4 PL JUSSIEU, F-75252 PARIS 05, FRANCE

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 28期

关键词：

(S)-PYROGLUTAMIC ACID; CYCLIC BETA-ENAMINO ESTER; CYCLIC BETA-AMINO ALCOHOL; STABILIZED YLIDS; ENANTIOSPECIFIC IMINIUM REDUCTION; ENANTIOSELECTIVE TOTAL SYNTHESIS; STEREOSELECTIVE SYNTHESIS; (+/-)-MONOMORINE-I; (+)-MONOMORINE-I;

D O I：

10.1016/S0040-4039(00)92707-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe the total synthesis of (+) Monomorine I 1 and the preparation of cis-2,5-disubstituted functionalized pyrrolidines via cyclic beta-enamino esters 4, starting from (S)-pyroglutamic acid.

引用

页码：3365 / 3368

页数：4

共 17 条

[1]

CELERIER JP, 1989, ORG SYNTH, V67, P170

[2]

CLEMENT JL, 1984, Patent No. 6980

[3]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[4] AN ALTERNATIVE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-MONOMORINE-I [J].

ITO, M ;

KIBAYASHI, C .

TETRAHEDRON LETTERS, 1990, 31 (35) :5065-5068

[5] A SHORT, SIMPLE SYNTHESIS OF (+/-)-MONOMORINE [J].

JEFFORD, CW ;

TANG, Q ;

ZASLONA, A .

HELVETICA CHIMICA ACTA, 1989, 72 (08) :1749-1752

[6]

Jones T.H., 1983, ALKALOIDS CHEM BIOL, V1, P33

[7]

MOMOSE T, 1990, CHEM PHARM BULL, V38, P2072

[8] STEREOSELECTIVE FORMAL SYNTHESIS OF (+/-)-MONOMORINE-I FROM 6-METHYL-2-PIPERIDINONE [J].

NAGASAKA, T ;

KATO, H ;

HAYASHI, H ;

SHIODA, M ;

HIKASA, H ;

HAMAGUCHI, F .

HETEROCYCLES, 1990, 30 (01) :561-566

[9] SYNTHESIS OF ISOMERS OF 3-BUTYL-5-METHYLOCTAHYDROINDOLIZINE, A TRAIL PHEROMONE OF PHARAOH ANT [J].

OLIVER, JE ;

SONNET, PE .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (17) :2662-2663

[10] ASYMMETRIC-SYNTHESIS .2. PRACTICAL METHOD FOR THE ASYMMETRIC-SYNTHESIS OF INDOLIZIDINE ALKALOIDS - TOTAL SYNTHESIS OF (-)-MONOMORINE-I [J].

ROYER, J ;

HUSSON, HP .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (05) :670-673

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