Palladium catalysed tandem cyclisation-anion capture.: Part 6:: Synthesis of sugar, nucleoside, purine, benzodiazepinone and β-lactam analogues via capture of in situ generated vinylstannanes

被引：33

作者：

Casaschi, A ^{[1
]}

Grigg, R ^{[1
]}

Sansano, JM ^{[1
]}

机构：

[1] Univ Leeds, Mol Innovat Divers & Automated Synthesis Ctr, Leeds LS2 9JT, W Yorkshire, England

来源：

TETRAHEDRON | 2000年 / 56卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

cascade reactions; palladium catalysis; hydrostannylation; Stille coupling; cyclisation;

D O I：

10.1016/S0040-4020(00)00661-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The regioselective palladium catalysed hydrostannylation of alkynes bearing a beta-heteroatom affords mainly alpha-vinyltin(IV) compounds that are used as terminating species in palladium catalysed cyclisation-anion capture processes. The pharmacophore attached to the alkyne moiety permits the synthesis of sugars, nucleosides, purines, benzodiazepinones and beta-lactams analogues in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7553 / 7560

页数：8

共 19 条

[1] SYNTHESIS AND RESOLUTION OF 3-AMINO-1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONES
BOCK, MG
DIPARDO, RM
EVANS, BE
RITTLE, KE
VEBER, DF
FREIDINGER, RM
HIRSHFIELD, J
SPRINGER, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) : 3232 - 3239
[2] Palladium catalysed cascade hydrostannylation-bis-cyclisation-intramolecular anion capture, routes to bridged- and spiro-cyclic small and macrocyclic heterocycles.
Casaschi, A
Grigg, R
Sansano, JM
Wilson, D
Redpath, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (25) : 4413 - 4416
[3] Palladium catalysed tandem cyclisation-anion capture. Part 5: Cascade hydrostannylation-bis-cyclisation-intramolecular anion capture. Synthesis of bridged- and spiro-cyclic small and macrocyclic heterocycles
Casaschi, A
Grigg, R
Sansano, JM
Wilson, D
Redpath, J
[J]. TETRAHEDRON, 2000, 56 (38) : 7541 - 7551
[4] The intramolecular Stille reaction
Duncton, MAJ
Pattenden, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10): : 1235 - 1246
[5] Liquid phase synthesis of a peptidic nucleic acid dimer
Farese, A
Patino, N
Condom, R
Dalleu, S
Guedj, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (09) : 1413 - 1416
[6] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY
FARINA, V
KRISHNAN, B
MARSHALL, DR
ROTH, GP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) : 5434 - 5444
[7] LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS
FARINA, V
KRISHNAN, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9585 - 9595
[8] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING
FARINA, V
KAPADIA, S
KRISHNAN, B
WANG, CJ
LIEBESKIND, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) : 5905 - 5911
[9] Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[10] Palladium catalysed tandem cyclisation-anion capture processes. Part 4: Organotin(IV) transfer agents
Fretwell, P
Grigg, R
Sansano, JM
Sridharan, V
Sukirthalingam, S
Wilson, D
Redpath, J
[J]. TETRAHEDRON, 2000, 56 (38) : 7525 - 7539

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