Asymmetric synthesis of (+)- and (-)-eptazocine via an enzymatic reaction

被引：21

作者：

Shiotani, S ^{[1
]}

Okada, H ^{[1
]}

Yamamoto, T ^{[1
]}

Nakamata, K ^{[1
]}

Adachi, J ^{[1
]}

Nakamoto, H ^{[1
]}

机构：

[1] NICHIIKO PHARMACEUT CO LTD,RES LAB,NAMERIKAWA 936,JAPAN

来源：

HETEROCYCLES | 1996年 / 43卷 / 01期

关键词：

D O I：

10.3987/COM-95-7232

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from (R)-3-hydroxy-2-(p-methoxybenzyl)propyl acetate (R-(+)-4) prepared by enzymatic monoacetylation of 2-(p-methoxybenzyl)propane-1,3-diol (3) with lipase PS in the presence of vinyl acetate as an acetyl donor, lactones ((+)- and (-)-6) were obtained. Using the lactones, (+)- and (-)-eptazocine were synthesized.

引用

页码：113 / 126

页数：14

共 23 条

[1] PHARMACOLOGICAL ACTIONS OF THE RACEMIC AND THE ENANTIOMERIC 1,4-DIMETHYL-10-HYDROXY-2,3,4,5,6,7-HEXAHYDRO-1,6-METHANO-1H-4-BENZAZONINES (C-HOMOBENZOMORPHANS) [J].

ACETO, MD ;

HARRIS, LS ;

WOODS, JH ;

KATZ, JL ;

SMITH, CB ;

MEDZIHRADSKY, F ;

JACOBSON, AE ;

SHIOTANI, S .

JAPANESE JOURNAL OF PHARMACOLOGY, 1985, 39 (01) :7-19

[2] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].

CHEN, CS ;

SIH, CJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707

[3] TOTAL SYNTHESIS OF (S)-12-HYDROXY-5,8,14-CIS-10-TRANS-EICOSATETRAENOIC ACID (SAMUELSSONS HETE) [J].

COREY, EJ ;

NIWA, H ;

KNOLLE, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (06) :1942-1943

[4] SYNTHESIS AND ANALGESIC ACTIVITIES OF URINARY METABOLITES OF A NEW ANALGESIC (-)-1,4-DIMETHYL-10-HYDROXY-2,3,4,5,6,7-HEXAHYDRO-1,6-METHANO-1H-4-BENZAZONINE HYDROBROMIDE (L-ST-2121) IN RATS [J].

FUTSUKAICHI, O ;

HAYASHI, I ;

MIYAMURA, Y ;

KUROBE, A ;

NOZAWA, T ;

MIYAMOTO, S ;

SHIOTANI, S .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1980, 100 (05) :509-514

[5] SYNTHESIS AND REACTIVITY OF SOME 1-ALKYL-2-AZETIDINONES (N-ALKYL-BETA-LACTAMS) [J].

HOLLEY, RW ;

HOLLEY, AD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (06) :2124-2129

[6] 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

[7] AN EFFICIENT ENANTIOSELECTIVE TOTAL SYNTHESIS OF ANTITUMOR LIGNANS - SYNTHESIS OF ENANTIOMERICALLY PURE 4-HYDROXYALKANENITRILES VIA AN ENZYMATIC-REACTION [J].

ITOH, T ;

CHIKA, J ;

TAKAGI, Y ;

NISHIYAMA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5717-5723

[8] RESOLUTION OF RACEMIC MIXTURES VIA LIPASE CATALYSIS IN ORGANIC-SOLVENTS [J].

KIRCHNER, G ;

SCOLLAR, MP ;

KLIBANOV, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7072-7076

[9] MILD, RAPID AND SELECTIVE DEPROTECTION OF ACETYLATED CARBOHYDRATES AND PHENOLS WITH GUANIDINE [J].

KUNESCH, N ;

MIET, C ;

POISSON, J .

TETRAHEDRON LETTERS, 1987, 28 (31) :3569-3572

[10] PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS [J].

MIYASHITA, M ;

YOSHIKOSHI, A ;

GRIECO, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3772-3774

← 1 2 3 →