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

[11]

NISHIDE K, 1994, 14TH P ANN M PHARM S, P65

[12] SYNTHESIS OF SOME DE AND CDE RING ANALOGS OF CAMPTOTHECIN [J].

PLATTNER, JJ ;

GLESS, RD ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (24) :8613-&

[13] THE BIOCATALYTIC APPROACH TO THE PREPARATION OF ENANTIOMERICALLY PURE CHIRAL BUILDING-BLOCKS [J].

SANTANIELLO, E ;

FERRABOSCHI, P ;

GRISENTI, P ;

MANZOCCHI, A .

CHEMICAL REVIEWS, 1992, 92 (05) :1071-1140

[14] OPTICAL RESOLUTION OF SOME HOMOBENZOMORPHAN DERIVATIVES AND THEIR PHARMACOLOGICAL PROPERTIES [J].

SHIOTANI, S ;

KOMETANI, T ;

NOZAWA, T ;

KUROBE, A ;

FUTSUKAICHI, O .

JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (12) :1558-1560

[15] 10-HYDROXY-4-METHYL-2,3,4,5,6,7-HEXAHYDRO-1,6-METHANO-1H-4-BENZAZONINE"DERIVATIVES (HOMOBENZOMORPHANS) AS ANALGESICS [J].

SHIOTANI, S ;

KOMETANI, T ;

MITSUHASHI, K ;

NOZAWA, T ;

KUROBE, A ;

FUTSUKAICHI, O .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (06) :803-806

[16] ENANTIOCONTROLLED SYNTHESIS OF (+)-APHANORPHINE FROM (R)-O-BENZYLGLYCIDOL - ASSIGNMENT OF ABSOLUTE-CONFIGURATION [J].

TAKANO, S ;

INOMATA, K ;

SATO, T ;

OGASAWARA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) :1591-1592

[17] THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF NATURAL (-)-APHANORPHINE [J].

TAKANO, S ;

INOMATA, K ;

SATO, T ;

TAKAHASHI, M ;

OGASAWARA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (04) :290-292

[18] CATALYTIC ASYMMETRIC-SYNTHESIS OF BENZYLIC QUATERNARY CARBON CENTERS - AN EFFICIENT SYNTHESIS OF (-)-EPTAZOCINE (VOL 115, PG 8477, 1993) [J].

TAKEMOTO, T ;

SODEOKA, M ;

SASAI, H ;

SHIBASAKI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11207-11207

[19] CATALYTIC ASYMMETRIC-SYNTHESIS OF BENZYLIC QUATERNARY CARBON CENTERS - AN EFFICIENT SYNTHESIS OF (-)-EPTAZOCINE [J].

TAKEMOTO, T ;

SODEOKA, M ;

SASAI, H ;

SHIBASAKI, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8477-8478

[20]

TORISAWA Y, 1983, CHEM PHARM BULL, V31, P2607

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