SUBSTITUTION-REACTIONS OF 2-PHENYLSULFONYL-PIPERIDINES AND 2-PHENYLSULFONYL-PYRROLIDINES WITH CARBON NUCLEOPHILES - SYNTHESIS OF THE PYRROLIDINE ALKALOIDS NORRUSPOLINE AND RUSPOLINONE

被引：85

作者：

BROWN, DS ^{[1
]}

CHARREAU, P ^{[1
]}

HANSSON, T ^{[1
]}

LEY, SV ^{[1
]}

机构：

[1] IMPERIAL COLL SCI TECHNOL & MED, DEPT CHEM, S KENSINGTON, LONDON SW7 2AY, ENGLAND

来源：

TETRAHEDRON | 1991年 / 47卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)86388-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several 2-phenylsuphonyl-piperidines and -pyrrolidines were prepared from the corresponding N-acyl animals by treatment with benzenesulphinic acid. On reaction with various carbon nucleophiles these sulphones gave good yields of substitution products. Typical nucleophiles used in these studies were organometallic reagents derived from Grignard reagents and zinc halide together with silyl enol ethers, silyl ketene acetals, allylsilanes and trimethylsilyl cyanide in the presence of a Lewis acid. These methods were employed in the synthesis of two natural product alkaloids; Norruspoline (38) and Ruspolinone (40).

引用

页码：1311 / 1328

页数：18

共 69 条

[1] STEREOSPECIFIC AND REGIOSPECIFIC ALLYLATION OF 4-CHLOROAZETIDINONES WITH ALLYLSILANES - CONVERGENT SYNTHESIS OF A KEY INTERMEDIATE FOR (+)-THIENAMYCIN
ARATANI, M
SAWADA, K
HASHIMOTO, M
[J]. TETRAHEDRON LETTERS, 1982, 23 (38) : 3921 - 3924
[2] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING
ARSENIYADIS, S
HUANG, PQ
PIVETEAU, D
HUSSON, HP
[J]. TETRAHEDRON, 1988, 44 (09) : 2457 - 2470
[3] ARSENIYADIS S, 1990, TETRAHEDRON LETT, V31, P1775
[4] NEW SYNTHESIS OF PIPECOLIC ACID AND ANALOGS
ASHER, V
BECU, C
ANTEUNIS, MJO
CALLENS, R
[J]. TETRAHEDRON LETTERS, 1981, 22 (02) : 141 - 144
[5] CONCISE SYNTHESES OF 4-(ARYLCARBONYLMETHYL)-AZETIDIN-2-ONES AND RELATED SYSTEMS
BARRETT, AGM
QUAYLE, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (20) : 1076 - 1077
[6] SYNTHESIS, ANTINOCICEPTIVE ACTIVITY AND OPIOID RECEPTOR PROFILES OF TRANS-3-(OCTAHYDRO-2H-PYRANO[2,3-C]PYRIDIN-4A-YL)PHENOLS AND TRANS-3-(OCTAHYDRO-1H-PYRANO[3,4-C]PYRIDIN-4A-YL)PHENOLS
BAYS, DE
BROWN, DS
LLOYD, JE
MCELROY, AB
SCOPES, DIC
BIRCH, PJ
HAYES, AG
SHEEHAN, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07): : 1187 - 1200
[7] SYNTHESIS, ANTINOCICEPTIVE ACTIVITY AND OPIOID RECEPTOR PROFILES OF 3-(OCTAHYDRO-1H-PYRANO[4,3-C]PYRIDIN-8A-YL AND OCTAHYDRO-1H-THIOPYRANO[4,3-C]PYRIDIN-8A-YL)PHENOLS
BAYS, DE
BROWN, DS
BELTON, DJ
LLOYD, JE
MCELROY, AB
MEERHOLZ, CA
SCOPES, DIC
BIRCH, PJ
HAYES, AG
SHEEHAN, MJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (07): : 1177 - 1186
[8] SUBSTITUTION-REACTIONS OF 2-BENZENESULFONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES
BROWN, DS
BRUNO, M
DAVENPORT, RJ
LEY, SV
[J]. TETRAHEDRON, 1989, 45 (13) : 4293 - 4308
[9] DIRECT SUBSTITUTION OF 2-BENZENESULFONYL CYCLIC ETHERS USING ORGANOZINC REAGENTS
BROWN, DS
LEY, SV
[J]. TETRAHEDRON LETTERS, 1988, 29 (38) : 4869 - 4872
[10] BROWN DS, 1990, SYNLETT, P48

← 1 2 3 4 5 6 7 →