67225-47-2Relevant academic research and scientific papers
Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: Application to the synthesis of the californian red scale beetle pheromone
Hesse, Matthew J.,Butts, Craig P.,Willis, Christine L.,Aggarwal, Varinder K.
supporting information, p. 12444 - 12448 (2013/02/23)
E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF·3 H2O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF2/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle. Copyright
SYNTHESE STEREOSELECTIVE D'UNE COMPOSANTE DE LA PHEROMONE SEXUELLE DE "L'ECAILLE ROUGE DE CALIFORNIE" : L'ACETATE D'ISOPROPENYL-6 METHYL-3 DECADIENE-3,9 YLE (3Z,6R)
Baudouy, Rene,Prince, Philippe
, p. 2067 - 2074 (2007/10/02)
The stereospecific elaboration of the trisubstituted double bond of acetate 1, is realized by condensation of an α-silylaldimine with aldehide 5 prepared by regioselective ozonolysis of (+)-limonene.
NEW SYNTHESIS OF THE CALIFORNIA RED SCALE SEX PHEROMONE
Becker, D.,Sahali, Y.
, p. 4541 - 4546 (2007/10/02)
The target molecules 1 and 2 were synthesized from a common intermediate 6 prepared from (R)-Limonene.The first enantioselective synthesis of 2 is described.
ASYMMETRIC ADDITION OF 1-ALKENYLCOPPER REAGENTS TO CHIRAL ENOATES: ENANTIOSELECTIVE SYNTHESIS OF CALIFORNIA RED SCALE PHEROMONE.
Oppolzer, Wolfgang,Stevenson, Thomas
, p. 1139 - 1140 (2007/10/02)
nBu3P-stabilized 1-alkenylcopper reagents undergo efficient 1,4-additions to enoates 1 and 5.Thus, acids 3, 7 or alcohols 4, 8 were obtained in high e.e. with recovery of the auxiliary. 4d was converted to pure (-)-pheromone 13, and 8b gave bromide 14b.
A NEW SYNTHESIS OF CALIFORNIA RED SCALE PHEROMONE FROM S-(+)-CARVONE
Caine, Drury,Crews, Everett
, p. 5359 - 5362 (2007/10/02)
A Retroaldol-Wittig olefination of the S-(+)-carvone derivative 3 is used as a key step in the synthesis of pheromone 1.
