- Lewis Acid-Catalyzed Intramolecular [2 + 2] Cycloaddition of α-Ester-Substituted Conjugated Dienyl- And Trienylphosphonates. New Synthesis of Functionalized Cyclic Terpenoids
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α-Ester-substituted 1,3-dienylphosphonates 7 and 8, prepared by the Knoevenagel condensation, underwent intramolecular [2 + 2] cycloaddition in the presence of Lewis acid to form bicyclo[4.2.0] (26-57% yield) and bicyclo[3.2.0]skeleton (14-38% yield), respectively. Similar treatment of homologous 1,3-dienylphosphonate 11 and 1,3,5-trienylphosphonate 12 resulted in the formation of ionone derivatives (30-94% yield). The intramolecular cycloaddition reaction was applicable to several conjugated dienes bearing an ester group.
- Okauchi, Tatsuo,Kakiuchi, Toshihito,Kitamura, Naotaka,Utsunomiya, Tomohisa,Ichikawa, Junji,Minami, Toru
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- ANTINEOPLASTIC AND CURCUMIN DERIVATIVES AND METHODS OF PREPARATION AND USE
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This invention comprises antineoplastic curcumin derivatives and methods of preparation and use thereof. Note is made of the acylation product of the lithium enolate of β-ionone using the acid chloride, 2(E)-3-(2,6,6-trimethycyclohex-1-en-1-yl)propenoyl chloride derived from β-cyclocitral. Particular reference is made to the isomeric compound, 1-(2,6,6-trimethylcyclohex-2-en-1-yl)-7-(2,6,6-trimethylcyclohex-1-en-1-yl)- 1,6-heptadiene-3,5-dione.
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Page/Page column 9-10
(2010/11/28)
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- The enantiomers of Iralia: preparation and odour evaluation
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The enantiomers of methyl ionones 1 and 2 were prepared by an enzyme-catalysed approach. Their odour properties were evaluated by skilful perfumers.
- Abate, Agnese,Brenna, Elisabetta,Fuganti, Claudio,Malpezzi, Luciana,Serra, Stefano
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p. 1145 - 1153
(2008/02/10)
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- Model insect antifeedants. Synthesis of azadiradione fragments through acyl radicals cyclizations and stannane coupling reactions
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A diastereoselective and versatile synthesis of the model insect antifeedant 16 related to azadiradione has been achieved in nine steps starting from α-cyclocitral 1. The key steps involve intramolecular alkene addition of an acyl radical and a Stille coupling reaction of a vinyl iodide with a stannylfuran.
- Fernandez-Mateos, Alfonso,Coca, Gustavo Pascual,Gonzalez, Rosa Rubio,Hernandez, Carolina Tapia
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p. 4817 - 4828
(2007/10/03)
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- Synthesis of a CDE fragment of the insect antifeedant 12-hydroxyazadiradione
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A diastereoselective and versatile synthesis of the model insect antifeedant 23 related to 12-hydroxyazadiradione has been achieved in 11 steps starting from α-cyclocitral, 1. The key steps involve intramolecular 1,3-dipolar cycloaddition of a nitrile oxide and a Stille coupling reaction of a vinyl iodide with a stannylfuran.
- Fernandez-Mateos, Alfonso,Coca, Gustavo Pascual,Gonzalez, Rosa Rubio,Hernandez, Carolina Tapia
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p. 9097 - 9102
(2007/10/03)
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- REFORMATSKY REACTION USING Zn/Ag COUPLE
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The Reformatsky reaction is easy to run in ethereal solvents in the presence of Zn/Ag couple.From methyl γ-bromocrotonate and krtones, remified esters are fromed in refluxing Et2O, linear ones in refluxing THF.
- Bortolussi, Michel,Seyden-Penne, Jacqueline
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p. 2355 - 2362
(2007/10/02)
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