Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam.: Enantioselective synthesis of (S)-(+)-N-methylcalycotomine and (R)-(+)-xylopinine

被引:21
作者
Czarnocki, Z [1 ]
Arazny, Z [1 ]
机构
[1] Univ Warsaw, Dept Chem, PL-02093 Warsaw, Poland
关键词
D O I
10.3987/COM-99-8681
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Pictet-Spengler reaction of (2R)-N-glyoxyloylbornane-10,2-sultam with dopamine hydrochloride gave the condensation product, which was further converted into (S)-(+)-N)-methylcalycotomine and (R)-(+)-xylopinine of high enantiomeric purity.
引用
收藏
页码:2871 / 2879
页数:9
相关论文
共 22 条
[1]   ASYMMETRIC DIELS-ALDER REACTION OF 1-METHOXYBUTA-1,3-DIENE WITH (2R)-N-GLYOXYLOYLBORNANE-10,2-SULTAM [J].
BAUER, T ;
CHAPUIS, C ;
KOZAK, J ;
JURCZAK, J .
HELVETICA CHIMICA ACTA, 1989, 72 (03) :482-486
[2]  
Bravo P, 1998, EUR J ORG CHEM, V1998, P435, DOI 10.1002/(SICI)1099-0690(199803)1998:3<435::AID-EJOC435>3.0.CO
[3]  
2-2
[4]   A convergent enantioselective synthesis of the tetrahydroisoquinoline unit in the spiro ring of ecteinascidin 743 [J].
Corey, EJ ;
Gin, DY .
TETRAHEDRON LETTERS, 1996, 37 (40) :7163-7166
[5]   Asymmetric Friedel-Crafts reaction mediated by new chiral auxiliaries derived from (1S)-(-)-beta-pinene: Enantioselective synthesis of (-)-8-norethyl,1'-normethyl etodolac [J].
Costa, PRR ;
Cabral, LM ;
Alencar, KG ;
Schmidt, LL ;
Vasconcellos, MLAA .
TETRAHEDRON LETTERS, 1997, 38 (40) :7021-7024
[6]   Enantiospecific formation of trans 1,3-disubstituted tetrahydro-beta-carbolines by the Pictet-Spengler reaction and conversion of cis diastereomers into their trans counterparts by scission of the C-1/N-2 bond [J].
Cox, ED ;
Hamaker, LK ;
Li, J ;
Yu, P ;
Czerwinski, KM ;
Deng, L ;
Bennett, DW ;
Cook, JM ;
Watson, WH ;
Krawiec, M .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (01) :44-61
[7]   ENANTIOSELECTIVE SYNTHESIS OF ISOQUINOLINE ALKALOIDS [J].
CZARNOCKI, Z ;
MACLEAN, DB ;
SZAREK, WA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1986, 64 (11) :2205-2210
[8]  
CZARNOCKI Z, 1986, B SOC CHIM BELG, V95, P749
[9]   ENANTIOSELECTIVE SYNTHESIS OF 1-SUBSTITUTED TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACIDS [J].
CZARNOCKI, Z ;
SUH, D ;
MACLEAN, DB ;
HULTIN, PG ;
SZAREK, WA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (05) :1555-1561
[10]   Pictet-Spengler reaction of biogenic amines with (2R)-N-glyoxyloylbornane-10,2-sultam. Enantioselective synthesis of (S)-(+)-N-methylcalycotomine [J].
Czarnocki, Z ;
Mieczkowski, JB ;
Kiegiel, J ;
Arazny, Z .
TETRAHEDRON-ASYMMETRY, 1995, 6 (12) :2899-2902