103729-83-5Relevant articles and documents
A practical enantioselective synthesis of the cigarette beetle sex pheromone serricornin
Chan, Philip C.-M.,Chong, J. Michael,Kousha, Karim
, p. 2703 - 2714 (1994)
(4RS,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone (serricornin and its C4- epimer) may be prepared from oxazolidinone 5 in 8 steps with an overall yield of 33%.
Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone
Sabitha, Gowravaram,Srinivas, Chitti,Maruthi, Chittapragada,Yadav, Jhillu Singh
experimental part, p. 2071 - 2079 (2012/03/27)
The synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone is described as their acetates using a desymmetrization strategy as well as an Evans syn aldol strategy.
Small organic molecule in enantioselective, direct aldol reaction "in water"
Aratake, Seiji,Itoh, Takahiko,Okano, Tsubasa,Usui, Takahiro,Shoji, Mitsuru,Hayashi, Yujiro
, p. 2524 - 2526 (2008/02/11)
A small organic molecule, Pro-NH2, catalyzing the enantioselective aldol reaction "in water" not merely "in the presence of water" with good enantioselectivity has been discovered for the first time. The Royal Society of Chemistry.
Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters
Liu, Ji-Feng,Abiko, Atsushi,Pei, Zhonghua,Buske, Dana C.,Masamune, Satoru
, p. 1873 - 1876 (2007/10/03)
A new chiral reagent for syn-selective aldol reactions has been developed based on the recent finding that the stereochemistry of the boron-mediated aldol reaction of a carboxylic ester is controlled by the bulkiness of the alcohol moiety of the ester, by the proper choice of reagents, and by the enolization conditions. This readily available, inexpensive reagent has been utilized in studies directed towards the synthesis of the macrolide tedanolide.
A short formal synthesis of (-)-serricornine
Pilli,De Andrade
, p. 233 - 241 (2007/10/02)
A short and efficient formal synthesis of serricornine (1), the sex pheromone of Lasioderma serricorne F., is described. The homochiral aldol 5 is straightforwardly converted to tosylate 9 to give homochiral lactone 2a (6 steps. 22% overall yield from oxazolidinone 4), a known precursor of (-)-1.
NEW STEREOCONTROLLED APPROACH TO THE INSECT SEX PHEROMONE SERRICORNIN
Szurdoki, F.,Novak, L.,Baitz-Gacs, Eszter,Szantay, Cs.
, p. 303 - 309 (2007/10/02)
The (Z)-allylic alcohol 1 was subjected to Sharpless asymmetric epoxidation to give the key intermediate 2.Ring opening of the epoxide 2 afforded the diol 3, which was then converted to serricornin 4, the sex pheromone of the cigarette beetle (Lasioderma serricorne F.) by routine transformations.
CHIRALITY TRANSFER IN THE ESTER ENOLATE CLAISEN REARRANGEMENT OF (R)-1-METHYL-(E)-2-BUTENYL HYDROXYACETATE AND ITS APPLICATION TO THE STEREOCONTROLLED PHEROMONE SYNTHESIS
Fujisawa, Tamotsu,Tajima, Kazuhisa,Sato, Toshio
, p. 1669 - 1672 (2007/10/02)
The ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2- butenyl hydroxaacetate provides complete asymmetric transfer along with 98percent erythroselectivity to give (2R,3S)-2-hydroxy-3-methyl-(E)-4-hexenoic acid.Its synthetic utility is demonstrated by the stereocontrolled synthesis of optically active pheromones.
SYNTHESIS AND ABSOLUTE STEREOCHEMISTRY OF SERRICORNIN
Mori, Kenji,Nomi, Hiroko,Chuman, Tatsuji,Kohno, Masahiro,Kato, Kunio,Noguchi, Masao
, p. 3705 - 3712 (2007/10/02)
The absolute stereochemistry of serricornin (4,6-dimethyl-7-hydroxy-3-nonanone) was established as 4S, 6S, 7S by synthesizing both (4S, 6S, 7S)-isomer and its antipode.Only the natural enantiomer was bioactive.by
