ASPIDOSPERMA ALKALOIDS VIA CYCLIZATION OF SECODINE INTERMEDIATE - SYNTHESIS OF (+/-)-3-OXOVINCADIFFORMINE ETHYL-ESTER

被引:27
作者
DANIELI, B [1 ]
LESMA, G [1 ]
PALMISANO, G [1 ]
PASSARELLA, D [1 ]
SILVANI, A [1 ]
机构
[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,I-20133 MILAN,ITALY
关键词
D O I
10.1016/S0040-4020(01)81347-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(+/-)-3-oxovincadifformine ethyl ester 14 has been synthesized through an intramolecular [4 pi+2 pi] cycloaddition of the 3-oxosecodine 13 first prepared in turn from the enamide 10 by dehydrogenation with benzeneseleninic anhydride. An insight into the conversion of 10 into 13 was gained, resulting in the suggestion of a plausible mechanistic pathway.
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收藏
页码:6941 / 6954
页数:14
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共 41 条
[11]  
HERCOUET A, 1908, TETRAHEDRON, V37, P2867
[12]  
KALAUS G, 1990, HETEROCYCLES, V31, P1183
[13]   SYNTHESIS OF VINCA ALKALOIDS AND RELATED-COMPOUNDS .63. A NEW SYNTHETIC PATHWAY FOR PREPARING ALKALOIDS AND RELATED-COMPOUNDS WITH THE ASPIDOSPERMA SKELETON - TOTAL SYNTHESES OF (+/-)-VINCADIFFORMINE, (+/--TABERSONINE, AND (+/-)-3-OXOTABERSONINE [J].
KALAUS, G ;
GREINER, I ;
KAJTARPEREDY, M ;
BRLIK, J ;
SZABO, L ;
SZANTAY, C .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1434-1442
[14]   TOTAL SYNTHESES OF (+/-)-CEPHALOTAXINE AND (+/-)-8-OXOCEPHALOTAXINE [J].
KUEHNE, ME ;
BORNMANN, WG ;
PARSONS, WH ;
SPITZER, TD ;
BLOUNT, JF ;
ZUBIETA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3439-3450
[15]   STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .4. ALTERNATIVE ROUTE TO SECODINE INTERMEDIATES PROVIDING SYNTHESES OF MINOVINE, VINCADIFFORMINE, ERVINCEINE, AND N(A)-METHYLERVINCEINE [J].
KUEHNE, ME ;
HUEBNER, JA ;
MATSKO, TH .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2477-2480
[16]   FORMATION OF D-NOR ASPIDOSPERMA ALKALOIDS BY CONDENSATION OF N(B)-BENZYLINDOLOAZEPINE WITH ALDEHYDES [J].
KUEHNE, ME ;
KUEHNE, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :4147-4148
[17]   STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .2. SYNTHESIS OF VINCADIFFORMINE FROM TETRAHYDRO-BETA-CARBOLINE THROUGH A SECODINE INTERMEDIATE [J].
KUEHNE, ME ;
ROLAND, DM ;
HAFTER, R .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3705-3710
[18]   STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .10. THE SYNTHESIS OF A 19-OXOSECODINE AND ITS CYCLIZATION TO MINOVINCINE [J].
KUEHNE, ME ;
EARLEY, WG .
TETRAHEDRON, 1983, 39 (22) :3715-3717
[19]   STUDIES IN BIOMIMETIC ALKALOID SYNTHESES .14. CONTROLLED, SELECTIVE SYNTHESES OF CATHARANTHINE AND TABERSONINE, AND RELATED DESETHYL COMPOUNDS, THROUGH GENERATION OF 15-OXOSECODINE INTERMEDIATES [J].
KUEHNE, ME ;
BORNMANN, WG ;
EARLEY, WG ;
MARKO, I .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :2913-2927
[20]  
LEMEN J, 1965, EXPERIENTIA, V21, P508