Parallel solution-phase syntheses of functionalised bicyclo[2.2.2]octanes: generation of a library using orchestrated multi-step sequences of polymer-supported reagents and sequesterants

被引：22

作者：

Ley, SV ^{[1
]}

Massi, A ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 21期

关键词：

D O I：

10.1039/b003129l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An array of bicyclo[2.2.2]octane derivatives was prepared in high yield using an orchestrated multi-step sequence of polymer-supported reagents and sequestering agents, without any chromatographic purification steps. Nine intermediate libraries were synthesised, with the final library possessing five sites of diversity. Key steps included an efficient tandem Michael addition reaction of acrylates with cyclohexenones and a subsequent reductive amination reaction.

引用

页码：3645 / 3654

页数：10

共 56 条

[41] BASE HYDROLYSIS OF HALOLACTONES IN THE BICYCLO(2.2.1)HEPTYL AND BICYCLO(2.2.2)OCTYL SYSTEMS
MORIARTY, RM
ADAMS, TB
[J]. TETRAHEDRON, 1979, 35 (19) : 2225 - 2235
[42] OBRECHT D, 1998, SOLID SUPPORTED COMB
[43] Combinatorial synthetic design
Oliver, SF
Abell, C
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (03) : 299 - 306
[44] Solution-phase chemical library synthesis using polymer-assisted purification techniques
Parlow, JJ
Devraj, RV
South, MS
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 1999, 3 (03) : 320 - 336
[45] The use of anion exchange resins for the synthesis of combinatorial libraries containing aryl and heteroaryl ethers
Parlow, JJ
[J]. TETRAHEDRON LETTERS, 1996, 37 (30) : 5257 - 5260
[46] PARLOW JJ, 1995, MOL DIVERS, V1, P266
[47] Arylsulfonate esters in solid phase organic synthesis. I. Cleavage with amines, thiolate, and imidazole
Rueter, JK
Nortey, SO
Baxter, EW
Leo, GC
Reitz, AB
[J]. TETRAHEDRON LETTERS, 1998, 39 (09) : 975 - 978
[48] Multiple parallel synthesis of N,N-dialkyldipeptidylamines as N-type calcium channel blockers
Ryder, TR
Hu, LY
Rafferty, MF
Millerman, E
Szoke, BG
Tarczy-Hornoch, K
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) : 1813 - 1818
[49] Shuttleworth SJ, 2000, SYNTHESIS-STUTTGART, P1035
[50] Shuttleworth SJ, 1997, SYNTHESIS-STUTTGART, P1217

← 1 2 3 4 5 6 →