- METHOD FOR PRODUCING MONOTERPENE AND MONOTERPINOID COMPOUNDS AND USE THEREOF
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In various embodiments, the present disclosure provides a method and enzyme for forming various compounds, such as monoterpenes and monoterpenoid compounds. In a specific example, the present disclosure provides a method for producing one or more of (?)-ipsdienol, (?)-ipsenol, ipsenone, and ipsdienone. The present disclosure also provides methods of using compounds formed from the disclosed method and enzyme.
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Page/Page column 1; 2; 4; 5
(2012/05/07)
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- Allylsilane-vinylcopper reagents: Palladium-mediated coupling with alkenyl halides. Synthesis and photochemical [2+2] cyclization of (±)-Ipsdienol
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Reaction of phenyldimethylsilyl-copper with 1,2-propadiene followed by Pd0 catalyzed coupling of the resulting copper intermediate with alkenyl halides affords allylsilane-containing dienes in high yield. Coupling with vinyl bromide gives 2-phenyldimethylsilylmethylbuta-1,3-diene which is an isoprenyl building block for the synthesis of (±)-Ipsenol and (±)-Ipsdienol, the aggregation pheromones of the Ips bark beetle. The photochemical [2+2] cyclization of Ipsdienol was also studied.
- Barbero,García,Pulido
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p. 824 - 826
(2007/10/03)
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- Claisen Rearrangements with Mesityl Oxide Dimethyl Ketal. Synthesis of Ipsdienone, E- and E-Ocimenone, 2,6-Dimethyl-2,7-octadien-4-one and 2,6-Dimethyl-2,7-octadien-4-ol
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4-Methyl-3-penten-2-one (mesityl oxide) dimethyl ketal was synthesized and utilizied in Claisen rearrangements with 2,3-butadien-1-ol and 2-buten-1-ol to form ipsdienone and 2,6-dimethyl-2,7-octadien-4-one, from which the ocimenones and 2,6-dimethyl-2,7-octadien-4-ol were prepared.
- Baekstroem, Peter,Stridh, Kjell,Li, Lanna,Norin, Torbjoern
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p. 442 - 447
(2007/10/02)
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- Terpenes and Terpene Derivatives, XVII. - Thermal and AlCl3-Catalyzed Reaction of Ocimenone
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Bis(trans-ocimenone) (5),reported to be a naturally occuring compound, is formed by thermal dimerization of (E)-ocimenone (E-4). - Treatment of 4 with AlCl3 leads, in addition to unchanged 4, to a mixture of the rearranged products filifolone (6) and rac-
- Weyerstahl, Peter,Zombik, Winfried,Gansau, Christian
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p. 422 - 427
(2007/10/02)
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- New Three-Step Syntheses of Racemic and Optically Active Ipsdienol from Myrcene
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2-Methyl-6-methylene-3,7-octatriene-2-ol(6), which is readily available from photooxidation of myrcene (5), was transformed into racemic and optically active ipsdienol (2).Treatment of the trienol 6 with perchloric acid in acetic acid yielded ipsdienyl acetate which on hydrolysis gave racemic ipsdienol (2) in 83percent overall yield.Oxidation of the trienol 6 with pyridinium chlorochromate in the presence of pyridine hydrochloride furnished 2-methyl-6-methylene-2,7-octadien-4-one (8) in 43percent yield.Reduction of this ketone with lithium aluminium hydride partially decomposed by one molar eg. each of ethanol and either (R)-(+)- or (S)-(-)- 2,2'-dihydroxy-1,1'-binaphthyl gave (R)-(-)- or (S)-(+)-ipsdienol (2' or 2", respectively) in 70percent yield and 60-65percent ee.
- Baeckstroem, P.,Bjoerkling, F.,Hoegberg, H.-E.,Norin, T.
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- CONDENSATION DES NITRILES AVEC LES ORGANOZINCIQUES ALLYLIQUES. APPLICATIONS EN SERIE TERPENIQUE
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The reaction of 3-bromomethyl-2,5-dihydrothiophen-1,1-dioxide 6 and 2-bromomethyl-1,3-butadiene 7 with nitriles in the presence of the zinc-silver couple leads to a mixture of ketones 8,9, the pyrolysis of which give the ketones 10 and 11, corresponding respectively to acylation of isoprene at its methyl group from 8, and at C-3 from 9.The reaction of bromide 7 with nitriles leads also to the formation of ketones 10 which by acid isomerisation give the ketones 12 corresponding to an acylation at C-1 of isoprene.In the same way the reaction of 2-(1'-methyl-4'-cyclohexenyl)-3-bromo propene 13 with 3,3-dimethyl acrylonitrile give β- atlantone 14 which is isomerised in acidic medium to α-atlantone 15. 10,11-dihydro α and β-atlantone 16, 17 are obtained by the same procedure from 13 and 3-methyl butyronitrile.
- Rousseau, G.,Drouin, J.
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p. 2307 - 2310
(2007/10/02)
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- CHEMISTRY OF THE ORGANOSILICON COMPOUNDS-165 2-TRIMETHYLSILYL-METHYL-1, 3-BUTADIENE-A VERSATILE BUILDING BLOCK FOR TERPENE SYNTHESIS
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Two types of synthetically useful reactions of 2-trimethylsilylmethyl-1,3-butadiene (7) are discussed.Reactions of 7 with acid chlorides, aldehydes, ketones and acetals activated by a Lewis acid give isoprenylated compounds, while 7 undergoes the Diels-Alder reaction whit dienophiles.High regiospecificity of the reaction qualifies 7 for a versatile building block of terpene synthesis.
- Sakurai, Hideki,Hosomi, Akira,Saito, Masaki,Sasaki, Koshi,Iguchi, Hirokazu,et al.
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p. 883 - 894
(2007/10/02)
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