FUNCTIONALIZED 2-AZABICYCLO(3.3.1)NONANES .17. STUDIES ON THE SYNTHESIS OF 8-ALKYL-8-ARYL-2-AZABICYCLO[3.3.1]NONAN-7-ONES - A SHORT SYNTHETIC ROUTE TO FUNCTIONALIZED 8-ALKYL DERIVATIVES

被引：6

作者：

BONJOCH, J

CASAMITJANA, N

QUIRANTE, J

GARRIGA, C

BOSCH, J

机构：

[1] Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona

来源：

TETRAHEDRON | 1992年 / 48卷 / 15期

关键词：

2-CYANOPIPERIDINE; MODIFIED POLONOVSKI REACTION; 2-AZABICYCLO[3.3.1]NONAN-7-ONES; WADSWORTH-EMMONS CONDENSATION; 5-FUNCTIONALIZED 2-OXOPENTYL SYNTHON;

D O I：

10.1016/S0040-4020(01)92254-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two approaches to 8-alkyl-8-aryl-2-azabicyclo[3.3.1]nonan-7-ones are explored. They are based on the cyclization of an alpha-alkyl alpha-aryl ketone upon an iminium salt generated from 2-cyanopiperidine 13 and on the arylation of 8-alkyl-2-azabicyclo[3.3.1]nonan-7-one 20. An efficient, short synthetic route to 8-alkyl-2-azabicyclo[3.3.1]nonan-7-ones, using phosphonate 16 as a 5-functionalized 2-oxopentyl synthon, is reported.

引用

页码：3131 / 3138

页数：8

共 16 条

[1] A NEW SYNTHETIC ENTRY TO PENTACYCLIC STRYCHNOS ALKALOIDS - TOTAL SYNTHESIS OF (+/-)-TUBIFOLIDINE, (+/-)-TUBIFOLINE, AND (+/-)-19,20-DIHYDROAKUAMMICINE
AMAT, M
LINARES, A
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6299 - 6312
[2] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS
BLECHERT, S
[J]. SYNTHESIS-STUTTGART, 1989, (02): : 71 - 82
[3] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .7. A NEW SYNTHESIS OF 4-AZATRICYCLO[5.2.2.04,8]UNDECAN-11-ONE
BONJOCH, J
CASAMITJANA, N
QUIRANTE, J
TORRENS, A
PANIELLO, A
BOSCH, J
[J]. TETRAHEDRON, 1987, 43 (02) : 377 - 381
[4] FUNCTIONALIZED 2-AZABICYCLO(3.3.1)NONANES .14. 8-ARYL-2-AZABICYCLO[3.3.1]NONAN-7-ONES - SYNTHESIS AND RETRO-MICHAEL RING-OPENING
BONJOCH, J
QUIRANTE, J
SOLE, D
CASTELLS, J
GALCERAN, M
BOSCH, J
[J]. TETRAHEDRON, 1991, 47 (25) : 4417 - 4428
[5] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .6. STUDIES DIRECTED TO THE SYNTHESIS OF PENTACYCLIC STRYCHNOS INDOLE ALKALOIDS
BONJOCH, J
CASAMITJANA, N
QUIRANTE, J
RODRIGUEZ, M
BOSCH, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) : 267 - 275
[6] FUNCTIONALIZED 2-AZABICYCLO[3.3.1]NONANES .9. SYNTHETIC ENTRY TO 8-(ORTHO-NITROPHENYL)-2-AZABICYCLO[3.3.1]NONAN-7-ONES - INTERMEDIATES FOR THE SYNTHESIS OF STRYCHNOS-TYPE SYSTEMS
BONJOCH, J
QUIRANTE, J
RODRIGUEZ, M
BOSCH, J
[J]. TETRAHEDRON, 1988, 44 (07) : 2087 - 2092
[7] Bosch J., 1988, STUDIES NATURAL PROD, VI, P31
[8] CASAMITJANA N, UNPUB TETRAHEDRON LE
[9] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .22. NEW APPROACH TO STRYCHNOS ALKALOIDS - STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE
FEVIG, JM
MARQUIS, RW
OVERMAN, LE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) : 5085 - 5086
[10] Grierson D., 1990, ORG REACTIONS, V39, P85, DOI DOI 10.1002/0471264180.OR039.02

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