62952-33-4Relevant academic research and scientific papers
Total Synthesis of (-)-Xylogranatopyridine B via a Palladium-Catalyzed Oxidative Stannylation of Enones
Schuppe, Alexander W.,Huang, David,Chen, Yifeng,Newhouse, Timothy R.
supporting information, p. 2062 - 2066 (2018/02/19)
We report a total synthesis of the pyridine-containing limonoid alkaloid (-)-xylogranatopyridine B in 11 steps from commercially available dihydrocarvone. The central pyridine ring was assembled by a late-stage fragment coupling approach employing a modified Liebeskind pyridine synthesis. One fragment was prepared by an allyl-palladium catalyzed oxidative enone β-stannylation, in which the key bimetallic β-stannyl palladium enolate intermediate undergoes a β-hydride elimination. This methodology also allowed introduction of alkyl and silyl groups to the β-position of enones.
Br?nsted Acid Catalysis in Visible-Light-Induced [2+2] Photocycloaddition Reactions of Enone Dithianes
Brenninger, Christoph,P?thig, Alexander,Bach, Thorsten
supporting information, p. 4337 - 4341 (2017/04/04)
1,3-Dithiane-protected enones (enone dithianes) were found to undergo an intramolecular [2+2] photocycloaddition under visible-light irradiation (λ=405 nm) in the presence of a Br?nsted acid (7.5–10 mol %). Key to the success of the reaction is presumably the formation of colored thionium ions, which are intermediates of the catalytic cycle. Cyclobutanes were thus obtained in very good yields (78–90 %). It is also shown that the dithiane moiety can be reductively or oxidatively removed without affecting the photochemically constructed ring skeleton.
Palladium-Catalyzed α-Arylation of Vinylogous Esters for the Synthesis of γ,γ-Disubstituted Cyclohexenones
Johnson, Thomas,Pultar, Felix,Menke, Friedericke,Lautens, Mark
supporting information, p. 6488 - 6491 (2016/12/23)
A palladium-catalyzed α-arylation of cyclic vinylogous esters to form products that are converted in one step to γ-alkyl-γ-aryl-substituted cyclohexenones is reported. This Pd-catalyzed reaction proceeds at room temperature, is generally high-yielding, and uses an amount of a commercially available catalyst as low as 0.25 mol %. The scope of aryl bromides is particularly broad, and alkenyl bromides can also be used. This two-step protocol, comprising α-arylation and reductive transposition, can be performed in one pot and is applicable to gram-scale synthesis.
Asymmetric allylic alkylation of cyclic vinylogous esters and thioesters by Pd-catalyzed decarboxylation of enol carbonate and β-ketoester substrates
Trost, Barry M.,Bream, Robert N.,Xu, Jiayi
, p. 3109 - 3112 (2007/10/03)
(Chemical Equation Presented) Excellent yields and enantioselectivities were achieved for the palladium-catalyzed asymmetric allylic alkylation of vinylogous thioesters. The close-to-neutral reaction conditions ensure that this reaction can tolerate a wide range of functionalities. Furthermore, this approach provides a convenient protocol for the synthesis of synthetically important α,α- and γ,γ-di-substituted cycloalkenones.
PROCESS FOR PRODUCING CYCLOHEXENONE LONG-CHAIN ALCOHOLS
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Page 14-15, (2010/02/08)
A process for producing cyclohexenone long-chain alcohol represented by the following formula (1): (wherein A represents a C10-C18 alkylene or alkenylene group, and each of R1, R2, and R3 individually represents hydrogen o
Pyrazolopyridine cycloalkanones and process for their preparation
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, (2008/06/13)
Novel tetrahydropyrazolo-[3,4-b]quinolinones, cyclopenta[b]pyrazolo-[4,3-e]pyridinones and cyclohepta[b]-pyrazolo[4,3-e]pyridinones, useful as anxiolytics having reduced side effects, are disclosed, including methods of preparation, pharmaceutical compositions containing them and intermediates used in their preparation.
Total Synthesis of (+/-)-Isocomene and Related Studies
Pirrung, Michael C.
, p. 82 - 87 (2007/10/02)
The total synthesis of the tricyclic sesquiterpene isocomene is described.The key bond forming reaction involves an intramolecular photocyloaddition to give tricyclo1,6>undecanone 6.Two routes are described from 6 to isocomene.The first involves acid-catalyzed rearrangement to tricyclo1,5>undecanone 7, addition of MeLi, and solvolysis, while the second uses a Wittig reaction followed by acid-catalyzed rearrangement.The question of maximum continuous orbital overlap in cyclobutyl carbinyl cation rearrangements is discussed, and certain stereochemical effects are found.
