Enzymatic asymmetrisation of prochiral alpha,alpha-disubstituted-malonates and -1,3-propanediols: Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine

被引：39

作者：

Fadel, A

Arzel, P

机构：

[1] Lab. des Carbocycles (Associe Au C., I.C.M.O. Bât. 420, Université de Paris-Sud

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(96)00538-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine are reported via the two key intermediates 3a and 3b obtained in 94-97% ee, from the readily available chirons (R)-5 and (R)-9. Which resulting from enzyme-catalysed asymmetrisation of prochiral alpha,alpha-disubstituted-1,3-propanediols and -malonates respectively. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：371 / 374

页数：4

相关论文

共 23 条

[11]

HALLINAN KO, 1995, TETRAHEDRON, V51, P12211

[12] 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

[13] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[14] METHODOLOGY FOR THE CONSTRUCTION OF QUATERNARY CARBON CENTERS [J].

MARTIN, SF .

TETRAHEDRON, 1980, 36 (04) :419-460

[15] Asymmetric syntheses of (-)-aphanorphine and (-)-eptazocine [J].

Node, M ;

Imazato, H ;

Kurosaki, R ;

Kawano, Y ;

Inoue, T ;

Nishide, K ;

Fuji, K .

HETEROCYCLES, 1996, 42 (02) :811-819

[16] BENZOMORPHANS - SYNTHESIS, STEREOCHEMISTRY REACTIONS, AND SPECTROSCOPIC CHARACTERIZATIONS [J].

PALMER, DC ;

STRAUSS, MJ .

CHEMICAL REVIEWS, 1977, 77 (01) :1-36

[17] 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

[18] Asymmetric synthesis of (+)- and (-)-eptazocine via an enzymatic reaction [J].

Shiotani, S ;

Okada, H ;

Yamamoto, T ;

Nakamata, K ;

Adachi, J ;

Nakamoto, H .

HETEROCYCLES, 1996, 43 (01) :113-126

[19] STUDIES ON STRUCTURE-ACTIVITY RELATIONSHIP OF ANALGETICS .17. SYNTHESES OF HOMOBENZOMORPHANS AND RELATED COMPOUNDS .2. [J].

SHIOTANI, S ;

KOMETANI, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1973, 21 (05) :1053-1060

[20] 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