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
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
收藏
页码:7553 / 7560
页数:8
相关论文
共 19 条
[1]   SYNTHESIS AND RESOLUTION OF 3-AMINO-1,3-DIHYDRO-5-PHENYL-2H-1,4-BENZODIAZEPIN-2-ONES [J].
BOCK, MG ;
DIPARDO, RM ;
EVANS, BE ;
RITTLE, KE ;
VEBER, DF ;
FREIDINGER, RM ;
HIRSHFIELD, J ;
SPRINGER, JP .
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. [J].
Casaschi, A ;
Grigg, R ;
Sansano, JM ;
Wilson, D ;
Redpath, 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 [J].
Casaschi, A ;
Grigg, R ;
Sansano, JM ;
Wilson, D ;
Redpath, J .
TETRAHEDRON, 2000, 56 (38) :7541-7551
[4]   The intramolecular Stille reaction [J].
Duncton, MAJ ;
Pattenden, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1235-1246
[5]   Liquid phase synthesis of a peptidic nucleic acid dimer [J].
Farese, A ;
Patino, N ;
Condom, R ;
Dalleu, S ;
Guedj, R .
TETRAHEDRON LETTERS, 1996, 37 (09) :1413-1416
[6]   PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].
FARINA, V ;
KRISHNAN, B ;
MARSHALL, DR ;
ROTH, GP .
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 [J].
FARINA, V ;
KRISHNAN, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9585-9595
[8]   ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING [J].
FARINA, V ;
KAPADIA, S ;
KRISHNAN, B ;
WANG, CJ ;
LIEBESKIND, LS .
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 [J].
Fretwell, P ;
Grigg, R ;
Sansano, JM ;
Sridharan, V ;
Sukirthalingam, S ;
Wilson, D ;
Redpath, J .
TETRAHEDRON, 2000, 56 (38) :7525-7539