Synthetic applications of 2-(1,3-dithian-2-yl)indoles .6. Synthesis of 20-epidasycarpidone

被引：38

作者：

Forns, P ^{[1
]}

Diez, A ^{[1
]}

Rubiralta, M ^{[1
]}

Solans, X ^{[1
]}

FontBardia, M ^{[1
]}

机构：

[1] UNIV BARCELONA,FAC FARM,LAB QUIM ORGAN,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON | 1996年 / 52卷 / 10期

关键词：

D O I：

10.1016/0040-4020(96)00033-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

20-Epidasycarpidone (10) and its N-benzyl analogue 9 have been synthesized via a conjugate addition of 2-(1,3-dithian-2-yl)indole (6) and 3-ethyl-Delta(3)-piperidein-2-ones 7 and 8, respectively. The transformation of 20-epidasycarpidone to 20-epiuleine (11) has been carried out as described in the literature in order to corroborate the structural assignments.

引用

页码：3563 / 3574

页数：12

共 17 条

[1] [Anonymous], INT TABLES XRAY CRYS
[2] BLECHERT S, 1995, SYNTHESIS-STUTTGART, P592
[3] STUDIES ON THE ULEINE ALKALOIDS .1. C-13 NMR-STUDIES ON ULEINE, 20-EPIULEINE AND (4S)-ULEINE-NB-OXIDE
BORRIS, RP
LANKIN, DC
CORDELL, GA
[J]. JOURNAL OF NATURAL PRODUCTS, 1983, 46 (02): : 200 - 205
[4] A REGIOSELECTIVE DIELS-ALDER SYNTHESIS OF ELLIPTICINE
DAVIS, DA
GRIBBLE, GW
[J]. TETRAHEDRON LETTERS, 1990, 31 (08) : 1081 - 1084
[5] SYNTHETIC APPLICATIONS OF 2-(1,3-DITHIAN-2-YL)INDOLES .4. NEW SYNTHESIS OF THE TETRACYCLIC ABED RING-SYSTEM OF STRYCHNOS ALKALOIDS
DIEZ, A
CASTELLS, J
FORNS, P
RUBIRALTA, M
GRIERSON, DS
HUSSON, HP
SOLANS, X
FONTBARDIA, M
[J]. TETRAHEDRON, 1994, 50 (22) : 6585 - 6602
[6] TOTAL SYNTHESIS OF (+/-)-DASYCARPIDONE, (+/-)-EPIDASYCARPIDONE, AND (+/-)-EPIULEINE
DOLBY, LJ
BIERE, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) : 3843 - &
[7] USE OF DIOXIRANES FOR THE CHEMOSELECTIVE OXIDATION OF TERTIARY-AMINES BEARING ALKENE MOIETIES
FERRER, M
SANCHEZBAEZA, F
MESSEGUER, A
DIEZ, A
RUBIRALTA, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (03) : 293 - 294
[8] TOTAL SYNTHESIS OF ULEINE-TYPE AND STRYCKNOS ALKALOIDS THROUGH A COMMON INTERMEDIATE
GRACIA, J
CASAMITJANA, N
BONJOCH, J
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) : 3939 - 3951
[9] SYNTHESES OF (+)-DASYCARPIDONE, (+)-3-EPI-DASYCARPIDONE, (+)-ULEINE AND (+)-3-EPI-ULEINE
JACKSON, A
WILSON, NDV
GASKELL, AJ
JOULE, JA
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (19): : 2738 - &
[10] STUDIES ON SYNTHESES OF HETEROCYCLIC COMPOUNDS .394. TOTAL SYNTHESES OF (+/-)-DASYCARPIDONE AND (+/-)-3-EPIDASYCARPIDONE - FORMAL TOTAL SYNTHESES OF (+/-)-ULEINE AND (+/-)-3-EPIULEINE
KAMETANI, T
SUZUKI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) : 1291 - &

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