A synthetic route to (+/-)-clavizepine through a dibenzoxepine intermediate

被引:13
作者
delaFuente, MC
Castedo, L
Dominguez, D
机构
[1] UNIV SANTIAGO,FAC QUIM,DEPT QUIM ORGAN,SANTIAGO COMPOSTE 15706,SPAIN
[2] CSIC,SECC ALCALOIDES,SANTIAGO COMPOSTE 15706,SPAIN
关键词
D O I
10.1021/jo960291n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new synthesis of (+/-)-clavizepine (1a), based on the dibenzoxepinediol 10 as main intermediate is described. The key step is the contraction of the oxepine ring to give the xanthene-9-carboxyaldehyde 11, on which the nitrogenated ring can be readily assembled.
引用
收藏
页码:5818 / 5822
页数:5
相关论文
共 15 条
[1]  
BOENTE JM, 1986, TETRAHEDRON LETT, V34, P4077
[2]   Total synthesis of (+/-)-O-methylclavizepine [J].
delaFuente, MC ;
Castedo, L ;
Dominguez, D .
TETRAHEDRON, 1996, 52 (13) :4917-4924
[3]  
GARCIA A, 1993, SYNLETT, P271
[4]   SYNTHESIS OF ALPHA-HYDROXY-TETRADEHYDROCULARINES [J].
GARCIA, A ;
CASTEDO, L ;
DOMINGUEZ, D .
TETRAHEDRON LETTERS, 1993, 34 (11) :1797-1798
[5]   TOTAL SYNTHESIS OF CULARINE ALKALOIDS VIA DIBENZOXEPINES AS KEY INTERMEDIATES [J].
GARCIA, A ;
CASTEDO, L ;
DOMINGUEZ, D .
TETRAHEDRON, 1995, 51 (31) :8585-8598
[6]   TOTAL SYNTHESIS OF (+/-)-CLAVIZEPINE [J].
ISHIBASHI, H ;
TAKAGAKI, K ;
IMADA, N ;
IKEDA, M .
TETRAHEDRON, 1994, 50 (34) :10215-10224
[7]  
ISHIBASHI H, 1994, SYNLETT, P49
[8]  
KAMETANI T, 1962, Yakugaku Zasshi, V82, P1307
[9]   BENZYNE CYCLIZATION ROUTE TO BENZO[C]PHENANTHRIDINE ALKALOIDS - SYNTHESIS OF CHELERYTHRINE, DECARINE, AND NITIDINE [J].
KESSAR, SV ;
GUPTA, YP ;
BALAKRISHNAN, P ;
SAWAL, KK ;
MOHAMMAD, T ;
DUTT, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1708-1713
[10]   REGIOSELECTIVE MONO-O-ALKYLATION OF SOME PYROCATECHOXIDE DIANIONS [J].
KESSAR, SV ;
GUPTA, YP ;
MOHAMMAD, T ;
GOYAL, M ;
SAWAL, KK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (07) :400-401