Deacetalisation-bicyclisation routes to novel polycyclic heterocycles using stannous chloride dihydrate

被引:16
作者
Cayley, Alex N.
Cox, Rhona J.
Menard-Moyon, Cecilia
Schmidt, Jan Peter
Taylor, Richard J. K. [1 ]
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] AstraZeneca R&D Charnwood, Med Chem, Loughborough LE11 5RH, Leics, England
关键词
heterocycles; stannous chloride; deacetalisation; bicyclisation;
D O I
10.1016/j.tetlet.2007.07.018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stannous chloride dihydrate-mediated deprotection-bicyclisation of a range of amides possessing a pendant acetal group is reported. These mild reaction conditions have been used to prepare a number of ring-fused heterocyclic compounds, some in enantiomerically pure form, which should be of interest both in their own right and as building blocks for the production of more complex target molecules. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6556 / 6560
页数:5
相关论文
共 15 条
[1]  
ARMORDE SM, 2005, ORG LETT, V7, P2031
[2]  
FAUL MM, 1995, ENCY REAGENTS ORGANI, V7, P4892
[3]   Synthesis of the integrastatin nucleus using the Ramberg-Bilcklund reaction [J].
Foot, JS ;
Giblin, GMP ;
Taylor, RJK .
ORGANIC LETTERS, 2003, 5 (23) :4441-4444
[4]   TIN(II) CHLORIDE DIHYDRATE - A MILD AND EFFICIENT REAGENT FOR CLEAVING ACETALS [J].
FORD, KL ;
ROSKAMP, EJ .
TETRAHEDRON LETTERS, 1992, 33 (09) :1135-1138
[5]   FORMATION OF CYCLOLS FROM N-HYDROXYACYLLACTAMS [J].
GRIOT, RG ;
FREY, AJ .
TETRAHEDRON, 1963, 19 (11) :1661-&
[6]   Construction of spiro-oxaquinolizidinone framework of Upenamide via organoiron complexes [J].
Han, Jeng Liang ;
Ong, Chi Wi .
TETRAHEDRON, 2007, 63 (03) :609-614
[7]   The combinatorial synthesis of bicyclic privileged structures or privileged substructures [J].
Horton, DA ;
Bourne, GT ;
Smythe, ML .
CHEMICAL REVIEWS, 2003, 103 (03) :893-930
[8]   Diastereoselective cationic tandem cyclizations to N-heterocyclic scaffolds:: Total synthesis of (-)-dysibetaine PP [J].
IJzendoorn, DR ;
Botman, PNM ;
Blaauw, RH .
ORGANIC LETTERS, 2006, 8 (02) :239-242
[9]  
MENDARDMOYON C, 2007, EUR J ORG CHEM, P3698
[10]   A FACILE SYNTHESIS OF CHIRAL BICYCLIC LACTAMS UTILIZED IN THE FORMATION OF CHIRAL QUATERNARY CARBON-COMPOUNDS [J].
MEYERS, AI ;
LEFKER, BA ;
SOWIN, TJ ;
WESTRUM, LJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4243-4246