29765-76-2Relevant academic research and scientific papers
Isoprenoid Chain Elongations by Claisen Rearrangements Using Acetals as Precursors of Vinyl Ethers
Baeckstroem, Peter,Li, Lanna
, p. 6521 - 6532 (1991)
Claisen rearrangements of allyl vinyl ethers, formed in situ by the acid catalyzed reaction of dimethyl acetals of acetaldehyde, acetone and isopropenyl methyl ketone with different types of allylic alcohols, have been compared.The primary, secondary and tertiary allylic alcohols used in the investigation were selected to serve as models for isoprenoid synthesis.The basis for two feasible methods that can be iterated to create isoprenoid chains has been investigated.
THE FORMATION AND SUBSEQUENT CYCLISATION OF NOVEL HYDROPEROXIDES FROM A 1,4- AND A 1,5-DIENE
Carless, Howard A.J.,Batten, Richard J.
, p. 4735 - 4738 (1982)
The preparation of the unsaturated hydroperoxides(3,4,5,6 and 7) by the sensitized photo-oxidation of the 1,4-diene(1) and the 1,5-diene(2) is described, together with the attempted free-radical cyclisation of these.
A study of epoxyolefin cyclizations catalyzed by bismuth trifluoromethanesulfonate and other metal triflates
Lacey, Joshua R.,Anzalone, Peter W.,Duncan, Christopher M.,Hackert, Matthew J.,Mohan, Ram S.
, p. 8507 - 8511 (2007/10/03)
Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cycli
Acyl radical-mediated polyene cyclisations directed towards steroid ring synthesis
Batsanov, Andrei,Chen, Ligong,Gill, G. Bryon,Pattenden, Gerald
, p. 45 - 56 (2007/10/03)
Treatment of appropriately substituted Se-phenyl 5,9,13-triene- and 5,9,13,17-tetraene-selenoates, i.e. 9b, 33, 40, 47a and 47b, with Bu3SnH-AIBN is found to lead to angular six-ring fused polycycles, viz. 20, 34, 50, 53 and 54 respectively, via consecuti
New radical mediated polyolefin cyclisations directed towards steroid ring synthesis
Chen, Ligong,Bryon Gill,Pattenden, Gerald
, p. 2593 - 2596 (2007/10/02)
Treatment of appropriately substituted 5,9-diene, 5,9,13-triene and 5,9,13,17-tetraene phenoselenyl esters, e.g. 1a, 9 and 14, with Bu3SnH-AIBN is shown to lead to linear and angular six-ring fused polycycles, viz 2, 11 and 15 respectively, via
Synthesis of 2,6-Dimethyl-1,6-heptadien-3-yl Acetate
Rao, E. Sreenivasa,Yadav, J. S.
, p. 1174 - 1175 (2007/10/02)
A convenient and short route for the synthesis of the title compound (4) starting from ethyl 2,6-dimethyl-3-oxo-hept-6-enoate (2) is described. 2 is treated with NaH in tetrahydrofuran and the resulting enolate on reduction with LAH affords the alcohol 2,
Synthesis of 2,6-Dimethyl-1,6-heptadien-3-ol Acetate, a Probable Biogenetic Precursor of the Pheromone, 2,6-Dimethyl-1,5-heptadien-3-ol Acetate
Shankaran, K.,Rao, A. S.
, p. 542 - 544 (2007/10/02)
Hydroxy acid (3b) which can be prepared in two steps from isopulegol has been acetylated to give 3,7-dimethyl-6-acetoxy-oct-7-enoic acid (3a).Oxidative decarboxylation of 3a furnishes 2,6-dimethyl-1,6-heptadien-3-ol acetate (2a) which is known to mimic the highly potent pheromone activity of 2,6-dimethyl-1,5-heptadien-3-olacetate (1) towards Comstock mealybug.A few analogues of 1 have been prepared.A possible biogenetic route for the formation of 1 involving 2a as intermediate is suggested.A new synthesis of keto acid (3g), whose enantiomer is naturally occuring has been carried out involving the steps 43e3g.
COPPER (I) CATALYSIS OF OLEFIN PHOTOREACTIONS -9. PHOTOBICYCLIZATION OF alpha -, beta -, AND gamma -ALKENYLALLYL ALCOHOLS.
Salomon,Coughlin,Ghosh,Zagorski
, p. 998 - 1007 (2007/10/14)
Cyclobutylcarbinyl alcohols of the bicyclo left bracket 3. 2. 0 right bracket heptane ring system are produced by UV irradiation of alpha -, beta -, and gamma -alkenylallyl alcohols in the presence of copper (I) trifluoromethanesulfonate (CuOTf). endo-2-Hydroxy epimers of bicyclo left bracket 3. 2. 0 right bracket heptan-2-ols are generated stereoselectively. This result as well as the effect of CuOTf on the **1H NMR spectrum of 4,4-dimethyl-1,6-heptadien-3-ol suggests that coordination of two C equals C bonds and the hydroxyl group with a single copper (I) is important. The derived bicyclo left bracket 3. 2. 0 right bracket heptan 2-ones fragment cleanly at 580 degree C to afford cyclopent-2-en-1-ones. Geometric isomerization competes with photobicyclization of (E)- and (Z)-octa-2,7-dien-1-ols.
Syntheses of 2,6-Dimethyl-1,5-heptadien-3-ol Acetate, the Pheromone of the Comstock Mealybug Pseudococcus comstocki Kuwana, and Its Analogs
Uchida, Minoru,Nakagawa, Kazuyuki,Negishi, Tsutomu,Asano, Shoji,Mori, Kenji
, p. 369 - 372 (2007/10/02)
The Comstock mealybug sex pheromone 2,6-dimethyl-1,5-heptadien-3-ol acetate and three analogs were synthesized and compared with natural material.
