Spirocyclization of an N-acyliminium ion with substituted pyridine: stereoselective synthesis of tetracyclic spirolactams possessing the pyridone nucleus

An efficient method for the stereoselective synthesis of tetracyclic spirolactams was developed based on a spirocyclization of an N-acyliminium ion with 2-methoxypyridine as the aromatic π-nucleophile.

[1]  H. Abe,et al.  Spirocyclization of an N-acyliminium ion with substituted pyridine: synthesis of tricyclic spirolactams possessing pyridine or pyridone nucleus , 2007 .

[2]  Maria M. M. Santos,et al.  Enantioselective spirocyclizations from tryptophanol-derived oxazolopiperidone lactams. , 2007, Organic letters.

[3]  H. Hamana,et al.  Hilbert-Johnson Reaction under High Pressure: A Facile Preparation of 2-Pyridones , 2007 .

[4]  A. Daïch,et al.  Intermolecular and intramolecular alpha-amidoalkylation reactions using bismuth triflate as the catalyst. , 2007, The Journal of organic chemistry.

[5]  Y. Tu,et al.  General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine. , 2006, Organic letters.

[6]  I. Turchi,et al.  Cyclizations of N-acyliminium ions. , 2004, Chemical reviews.

[7]  R. Prager,et al.  On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones , 2003 .

[8]  C. George,et al.  Synthesis, nicotinic acetylcholine receptor binding affinities, and molecular modeling of constrained epibatidine analogues. , 2003, Journal of medicinal chemistry.

[9]  W. Nico Speckamp,et al.  New developments in the chemistry of N-acyliminium ions and related intermediates. , 2000 .

[10]  S. Ikeda,et al.  Synthesis of A-ring fragments of 1α,25-dihydroxyvitamin D3 and taxane diterpenoids: Effective construction of conjugated formylcyclohexene frameworks from isoxazolines , 1998 .

[11]  A. Padwa,et al.  Electrophilic Aromatic Substitution on Pyridine Rings. Intramolecular Cyclization Using N-Acyliminium Ions , 1997 .

[12]  H. Mayr,et al.  REACTIONS OF ALLYLSILANES WITH IMINIUM SALTS : ENE REACTIONS WITH INVERSE ELECTRON DEMAND , 1996 .

[13]  D. Schinzer,et al.  Uses of Silicon-Containing Compounds in the Synthesis of Natural Products , 1995 .

[14]  Y. Langlois,et al.  Functionalisation of 2-Methoxy-6-methylpyridine , 1994 .

[15]  L. Overman,et al.  Asymmetric synthesis of either enantiomer of opium alkaloids and morphinans. Total synthesis of (-)- and (+)-dihydrocodeinone and (-)- and (+)-morphine , 1993 .

[16]  Davidr . Evans,et al.  A stereoselective synthesis of (.+-.)-H12-histrionicotoxin and related photoaffinity-labeled congeners , 1982 .

[17]  H. Hiemstra,et al.  Intramolecular reactions of N-acyliminium intermediates , 1985 .

[18]  H. Schoemaker,et al.  Stereocontrolled synthesis of functionalized 1-azaspirans , 1980 .

[19]  Davidr . Evans,et al.  A formal synthesis of (±)-perhydrohistrionicotoxin via α-acylimmonium ion-olefin cyclizations , 1979 .

[20]  H. Schoemaker,et al.  A novel synthetic approach to perhydrohistrionicotoxin stereoselective synthesis of 1-aza-spiranes , 1978 .