SYNTHETIC STUDIES ON THE GELSEMIUM ALKALOIDS

被引:11
作者
TAKAYAMA, H
SAKAI, S
机构
关键词
D O I
10.5059/yukigoseikyokaishi.48.876
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
From the medicinal plants Gelsemium, various skeletal type of indole alkaloids were isolated.Along the biogenetic speculation of these alkaloids, some of the structurally complex compounds, involving sarpagine-, humantenine-, koumine-, and gelsedine-type, were prepared from ajmaline and the Gardneriaalkaloids.In the second half of this article, recent synthetic studies on the sarpagine type alkaloids and on a principal Gelsemium alkaloid, gelsemine, are reviewed. © 1990, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.
引用
收藏
页码:876 / 890
页数:15
相关论文
共 44 条
[1]  
AIMI N, 1971, TETRAHEDRON LETT, P2061
[2]  
AIMI N, 1989, ALKALOIDS, V36, P1
[3]   A MILD AND STEREOSPECIFIC CONVERSION OF VICINAL DIOLS INTO OLEFINS VIA 2-METHOXY-1,3-DIOXOLANE DERIVATIVES [J].
ANDO, M ;
OHHARA, H ;
TAKASE, K .
CHEMISTRY LETTERS, 1986, (06) :879-882
[4]   INSITU PREPARATION OF (MU-CHLORO)(MU-METHYLENE)BIS(CYCLOPENTADIENYL)(DI-METHYLALUMINUM)TITANIUM (TEBBE REAGENT) [J].
CANNIZZO, LF ;
GRUBBS, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2386-2387
[5]   ALPHA-ACYLAMINO RADICAL CYCLIZATIONS - APPLICATION TO THE SYNTHESIS OF A TETRACYCLIC SUBSTRUCTURE OF GELSEMINE [J].
CHOI, JK ;
HA, DC ;
HART, DJ ;
LEE, CS ;
RAMESH, S ;
WU, S .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (02) :279-290
[6]   AN APPROACH TO THE SYNTHESIS OF GELSEMINE - THE INTRAMOLECULAR REACTION OF AN ALLYLSILANE WITH AN ACYLIMINIUM ION FOR THE SYNTHESIS OF ONE OF THE QUATERNARY CENTERS [J].
CLARKE, C ;
FLEMING, I ;
FORTUNAK, JMD ;
GALLAGHER, PT ;
HONAN, MC ;
MANN, A ;
NUBLING, CO ;
RAITHBY, PR ;
WOLFF, JJ .
TETRAHEDRON, 1988, 44 (13) :3931-3944
[7]   SYNTHESIS STUDIES DIRECTED TOWARD GELSEMINE - A NEW SYNTHESIS OF HIGHLY FUNCTIONALIZED CIS-HYDROISOQUINOLINES [J].
EARLEY, WG ;
JACOBSEN, EJ ;
MEIER, GP ;
OH, T ;
OVERMAN, LE .
TETRAHEDRON LETTERS, 1988, 29 (31) :3781-3784
[8]   SYNTHESIS STUDIES DIRECTED TOWARD GELSEMINE - PREPARATION OF AN ADVANCED PENTACYCLIC INTERMEDIATE [J].
EARLEY, WG ;
OH, T ;
OVERMAN, LE .
TETRAHEDRON LETTERS, 1988, 29 (31) :3785-3788
[9]   2 NEW STEREOCHEMICALLY COMPLEMENTARY OXINDOLE SYNTHESES [J].
FLEMING, I ;
LORETO, MA ;
MICHAEL, JP ;
WALLACE, IHM .
TETRAHEDRON LETTERS, 1982, 23 (19) :2053-2056
[10]   SYNTHETIC STUDIES TOWARD GELSEMINE .2. PREPARATION OF THE TETRACYCLIC SKELETAL PART BY WAY OF A HIGHLY STEREOSPECIFIC INTRAMOLECULAR REACTION OF A SILYL ENOL ETHER WITH AN N-ACYLIMINIUM ION [J].
HIEMSTRA, H ;
VIJN, RJ ;
SPECKAMP, WN .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3882-3884