A STRAIGHTFORWARD ENTRY TO THE ERVITSINE SKELETON - SYNTHESIS OF 16-DEMETHYLENEERVITSINE

被引：9

作者：

BENNASAR, ML ^{[1
]}

ZULAICA, E ^{[1
]}

VIDAL, B ^{[1
]}

BOSCH, J ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC PHARM,ORGAN CHEM LAB,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(00)74813-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A short synthetic route to 16-demethyleneervitsine (6), based on the nucleophilic addition of 2-acetyl-indole enolates to N-alkyl-beta-acylpyridinium salts and further acid cyclization of the resulting 1,4-dihydropyridine intermediates, is reported.

引用

页码：3895 / 3898

页数：4

共 15 条

[1] ANDRIANTSIFERANA M, 1977, TETRAHEDRON LETT, P2587
[2] BENNASAR ML, 1988, HETEROCYCLES, V27, P789
[3] GENERAL-METHOD FOR THE SYNTHESIS OF BRIDGED INDOLE ALKALOIDS - NUCLEOPHILIC-ADDITION OF INDOLEACETIC ESTER ENOLATES TO N-ALKYLPYRIDINIUM SALTS
BENNASAR, ML
ALVAREZ, M
LAVILLA, R
ZULAICA, E
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (04) : 1156 - 1168
[4] Bhandari K. S., 1971, CAN J CHEM, V49, P2354
[5] SYNTHETIC APPLICATIONS OF "2-CYANO-1,2,3,6-TETRAHYDROPYRIDINES .2. SYNTHESIS OF ISODASYCARPIDONE AND RELATED SYSTEMS, THE ERVITSINE SKELETON, AND ITS BENZO ANALOG
BOSCH, J
RUBIRALTA, M
DOMINGO, A
BOLOS, J
LINARES, A
MINGUILLON, C
AMAT, M
BONJOCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) : 1516 - 1522
[6] ELABORATION OF THE ETHYLIDENE SUBSTITUENT IN THE SYNTHESIS OF INDOLE ALKALOIDS
BOSCH, J
BENNASAR, ML
[J]. HETEROCYCLES, 1983, 20 (12) : 2471 - 2511
[7] SYNTHETIC APPLICATIONS OF 2-CYANO-1,2,3,6-TETRAHYDROPYRIDINES .3. SYNTHESIS OF 19,20-ISO-16-DEMETHYLENEERVITSINE
BOSCH, J
RUBIRALTA, M
BOLOS, J
[J]. TETRAHEDRON, 1987, 43 (02) : 391 - 396
[8] CHASTRET.F, 1970, B SOC CHIM FR, P1151
[9] 2-CYANO DELTA-3 PIPERIDEINES .9. GENERAL STRATEGIES FOR THE SYNTHESIS OF CORYNANTHE-STRYCHNOS TYPE INDOLE ALKALOIDS
GRIERSON, DS
HARRIS, M
HUSSON, HP
[J]. TETRAHEDRON, 1983, 39 (22) : 3683 - 3694
[10] 2-CYANO DELTA-3 PIPERIDINES .2. TOTAL SYNTHESIS IN THE (+/-) ERVITSINE ALPHA-ACYLINDOLE ALKALOID SERIES
HARRIS, M
GRIERSON, DS
RICHE, C
HUSSON, HP
[J]. TETRAHEDRON LETTERS, 1980, 21 (20) : 1957 - 1960

← 1 2 →