Asymmetric synthesis of benzylic quaternary carbon center via an enzymatic reaction

被引：34

作者：

Shiotani, S

Okada, H

Nakamata, K

Yamamoto, T

Sekino, F

机构：

[1] Department of Chemistry, Faculty of Science, Toyama University, Toyama 930

来源：

HETEROCYCLES | 1996年 / 43卷 / 05期

关键词：

D O I：

10.3987/COM-96-7421

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(R)-(+)-((R)-(+)-12) and (S)-(-)-1-formyl-1-methyl-7-methoxy-1,2,3,4-tetrahydronaphthalene ((S)-(-)-12) were synthesized based on enantioselective PLE hydrolysis of diethyl 2-(m-methoxyphenyl)-2-methylmalonate. From (R)-(+)-12, (+)-O-Methylaphanorphine (16) and (-)-aphanorphine were synthesized. (S)-(+)-1-(N-Acetyl-N-methylaminoethyl)-1-methyl-7-methoxytetralin (25) was synthesized from (S)-(-)-12. This transformation constitutes a formal synthesis of (-)-eptazocine.

引用

收藏

页码：1031 / 1047

页数：17

相关论文

共 19 条

[1] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - SELECTIVE AND VERSATILE TOTAL SYNTHESES OF THE ENANTIOMERS OF ALPHA-CUPARENONE AND BETA-CUPARENONE FROM A COMMON OPTICALLY-ACTIVE PRECURSOR [J].

CANET, JL ;

FADEL, A ;

SALAUN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (12) :3463-3473

[2] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - TOTAL SYNTHESES OF (+)-EPILAURENE AND (-)-ISOLAURENE [J].

FADEL, A ;

CANET, JL ;

SALAUN, J .

TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :27-30

[3] ASYMMETRIC CONSTRUCTION OF BENZYLIC QUATERNARY CARBONS FROM CHIRAL MALONATES - FORMAL SYNTHESIS OF NATURAL (-)APHANORPHINE [J].

FADEL, A ;

ARZEL, P .

TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :893-900

[4] A STEREOCONTROLLED ALKYLATION OF CHIRAL PYRIDINIUM SALTS WITH GRIGNARD-REAGENTS - SYNTHESIS OF (+)-NORMETAZOCINE AND (+)-NORDEXTRORPHAN [J].

GENISSON, Y ;

MARAZANO, C ;

DAS, BC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2052-2057

[5] APHANORPHINE, A NOVEL TRICYCLIC ALKALOID FROM THE BLUE-GREEN-ALGA APHANIZOMENON-FLOS-AQUAE [J].

GULAVITA, N ;

HORI, A ;

SHIMIZU, Y ;

LASZLO, P ;

CLARDY, J .

TETRAHEDRON LETTERS, 1988, 29 (35) :4381-4384

[6]

HALLINAN KO, 1995, TETRAHEDRON, V51, P12211

[7] POLYETHYLENE-GLYCOL MONOMETHYL ETHER-MODIFIED PIG-LIVER ESTERASE - PREPARATION, CHARACTERIZATION AND CATALYSIS OF ENANTIOSELECTIVE HYDROLYSIS IN WATER AND ACYLATION IN ORGANIC-SOLVENTS [J].

HEISS, L ;

GAIS, HJ .

TETRAHEDRON LETTERS, 1995, 36 (22) :3833-3836

[8] PREPARATION OF (R)-MEVALONIC AND (S)-MEVALONIC ACIDS [J].

HUANG, FC ;

LEE, LFH ;

MITTAL, RSD ;

RAVIKUMAR, PR ;

CHAN, JA ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4144-4145

[9] ASYMMETRIC-SYNTHESIS OF THE KEY INTERMEDIATES LEADING TO (-)-APHANORPHINE AND (-)-EPTAZOCINE [J].

HULME, AN ;

HENRY, SS ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1265-1270

[10] SYNTHESIS AND ANALGETIC ACTIVITY OF SOME BENZOMORPHAN ANALOGS [J].

KOMETANI, T ;

SHIOTANI, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (11) :1105-1110