A Bridgehead Enone Approach to Huperzine A. -Reaction of the monoacetal of 1,4-cyclohexanedione (I) with diphenyl disulfide (II) leads to the formation of the keto sulfide which is oxidized to give the sulfoxide (III). Cyclocondensation with methacrolein (IV) is followed by protection and Wittig reaction to produce the bicyclic ketone (VIII) after deprotection. Aminolysis of the latter yields the aminobicyclononanone (IX). -(KRAUS, G. A.; HANSEN, J.; VINES, D.; Synth. Commun. 22 (1992Commun. 22 ( ) 18, 2625Commun. 22 ( -2634 Dep.
Conjugate Addition Reactions of Metalated Alkyl Pyridines. A Direct Route to 6-Substituted Pyridones.-The reaction of metalated alkyl pyridines with α,β-unsaturated ketones yields 1,2-and/or 1,4-addition products. Deprotection of (VII) using fresh prepared Raney-Ni results in formation of the pyridone (IX), a type of compound required as structural subunit in many biologically active compounds. -(KRAUS, G. A.; VINES, D. R.; MALPERT, J. H.; Tetrahedron 51 (1995) 5, 1337-1344; Dep. Chem., Iowa State Univ., Ames, IA 50011, USA; EN)
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