- Radical reactions on pinene-oxide derivatives induced by Ti(III)
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A practical, brief and selective synthesis of several pinene oxide derived terpenoids can be achieved from readily available starting materials. The key step is a radical reaction promoted by titanocene chloride.
- Fernández-Mateos,Herrero Teijón,Rubio González
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supporting information; experimental part
p. 9529 - 9534
(2011/12/15)
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- Synthesis and AChE inhibitory activity of new chiral tetrahydroacridine analogues from terpenic cyclanones
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This work describes the enantioselective synthesis of a new series of terpenic chiral 9-aminotetrahydroacridine analogues. Several chiral ketones were synthesized from natural monoterpenes in an optically active form and subjected to the cyclodehydration reactions with anthranilonitrile in the presence of BF3·Et2O as catalyst. The 9-aminotetrahydroacridine analogues were tested as acetylcholinesterase (AChE) inhibitors. Based on qualitative structure-activity relationship some trends are suggested.
- Santos Pisoni, Diego dos,Sobieski da Costa, Jessé,Gamba, Douglas,Petzhold, Cesar Liberato,César de Amorim Borges, Antonio,Ceschi, Marco Antonio,Lunardi, Paula,Saraiva Gon?alves, Carlos Alberto
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scheme or table
p. 526 - 535
(2010/04/06)
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- Tetrasubstituted pyrrolidines via a tandem aza-Payne/hydroamination reaction
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A facile tandem aza-Payne/hydroamination reaction of aziridinol is reported, which yields highly functionalized pyrrolidines. Addition of alkynyl Grignards to 2,3-aziridinals yields, in most cases, high syn to anti ratios of the aziridinol. Treatment of the syn-aziridinol with base leads initially to an aza-Payne rearrangement, which juxtaposes the amine and the alkyne in favorable orientation to complete the hydroamination. The anti-aziridinol undergoes the aza-Payne rearrangement, but cannot proceed further with the hydroamination. Copyright
- Schomaker, Jennifer M.,Geiser, Andrea R.,Huang, Rui,Borhan, Babak
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p. 3794 - 3795
(2008/02/01)
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- Allyl sulfones as precursors to allylzincs in the palladium-catalyzed zinc-ene cyclization: Highly efficient synthesis of enantiopure (-)-erythrodiene
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(Chemical Equation Presented) Easily prepared allyl phenyl sulfones, capable of introduction of the alkene by electrophilic α-substitution, are superior to allyl acetates as substrates for Pd-catalyzed Zn-ene cyclizations, providing C5 or C4N r
- Deng, Kai,Chalker, Justin,Yang, Ao,Cohen, Theodore
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p. 3637 - 3640
(2007/10/03)
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- Synthesis of (-)-erythrodiene and (+)-7-epispirojatamol via intramolecular Pd-catalyzed allylzincation
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Two spirobicyclic sesquiterpenoids, (-)-erythrodiene (1) and (+)-7-epispirojatamol (30), were synthesized in enantiomericaliy pure form via an intramolecular allylzincation process. The allylzinc species were formed in the presence of Et2Zn via transmetallation of a catalytically generated allylpalladium intermediate. Several Pd catalysts were tested for this transformation, and [Pd(OAc)2]/Bu3P (1 equiv.) was found to be, by far, the most effective. Whereas the preparation of 1 involved allylzincation of a tethered terminal olefin, 30 was formed via a novel intramolecular allyl zincation of a methyl ketone. Both reactions showed the same stereochemical preference, yielding the spirobicyclic products in 95:5 and 4:1 diastereoisomer ratios, respectively.
- Oppolzer, Wolfgang,Flachsmann, Felix
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p. 416 - 430
(2007/10/03)
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- Synthesis of (-)-erythrodiene via intramolecular Pd-catalyzed Zn-ene reaction
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A highly diastereoselective synthesis of (-)-Erythrodiene was achieved via an intramolecular Pd-catalyzed Zne-ene reaction as the key step. It was found that Pd(OAc)2/Bu3P was a superior catalyst for this reaction to Pd(PPh3)4.
- Oppolzer,Flachsmann
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p. 5019 - 5022
(2007/10/03)
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