An efficient asymmetric synthesis of key intermediates in the synthesis of aphanorphine and eptazocine

被引:29
作者
Taylor, SK [1 ]
Ivanovic, M [1 ]
Simons, LJ [1 ]
Davis, MM [1 ]
机构
[1] Hope Coll, Dept Chem, Holland, MI 49422 USA
关键词
D O I
10.1016/S0957-4166(03)00117-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Efficient, formal syntheses of aphanorphine and eptazocine are reported that involve epoxide cyclizations. The necessary chiral epoxides were prepared following treatment of diols prepared by Sharpless asymmetric osmylations of an alkene. The cyclizations formed a ring compound with the same enantiomeric purity as the starting epoxide. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:743 / 747
页数:5
相关论文
共 28 条
[1]   PALLADIUM-CATALYZED POLYENE CYCLIZATIONS OF TRIENYL TRIFLATES [J].
CARPENTER, NE ;
KUCERA, DJ ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) :5846-5848
[2]   Facile one-pot epoxidation-nucleophilic opening sequence for vicinal diols [J].
Cink, RD ;
Forsyth, CJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) :8122-8123
[3]   AN EFFECTIVE SYSTEM FOR EPOXIDE-INITIATED CATION-OLEFIN CYCLIZATION [J].
COREY, EJ ;
SODEOKA, M .
TETRAHEDRON LETTERS, 1991, 32 (48) :7005-7008
[4]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[5]  
2-V
[6]  
El-Azab AS, 2002, HETEROCYCLES, V56, P39
[7]   Enzymatic asymmetrisation of prochiral alpha,alpha-disubstituted-malonates and -1,3-propanediols: Formal asymmetric syntheses of (-)-aphanorphine and (+)-eptazocine [J].
Fadel, A ;
Arzel, P .
TETRAHEDRON-ASYMMETRY, 1997, 8 (03) :371-374
[8]   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
[9]   Total synthesis of (±)-lennoxamine and (±)-aphanorphine by intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins [J].
Fuchs, JR ;
Funk, RL .
ORGANIC LETTERS, 2001, 3 (24) :3923-3925
[10]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066