82335-98-6Relevant academic research and scientific papers
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
, 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.
Synthesis of a biologically active analog of the sex pheromone of cigarette beetle (Lasioderma serricorne)
Lozanova,Stepanov,Veselovsky
, p. 1254 - 1257 (2007/10/03)
A simple synthesis of a diastereomeric mixture of 7-hydroxy-4,6- dimethylnonan-3-ones was carried out. In the biological action, it is an analog of serricornin, the sex pheromone of the cigarette beetle (Lasioderma serricorne).
Synthesis of (4R,6S,7R)-7-hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5-dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus
Masuda, Yui,Fujita, Ken,Mori, Kenji
, p. 1744 - 1750 (2007/10/03)
(4R,6S,7R)-7-Hydroxy-4,6-dimethyl-3-nonanone and (3R,5S,6R)-6-hydroxy-3,5- dimethyl-2-octanone, the pheromone components of the bostrychid beetle, Dinoderus bifoveolatus, as well as their (4R,6S,7S)-and (3R,5S,6S)-isomers were synthesized from (2R,4S,5R)- and (2R,4S,5S)2,4-dimethyl-5-heptanolide, respectively.
AN EFFICIENT AND STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-SERRICORNINE
Pilli, R. A.,Mutra, M. M.
, p. 981 - 994 (2007/10/02)
An efficient and stereoselective total synthesis of (+/-)-serricornine (1) the sex pheromone produced by the female cigarette beetle Lasioderma serricorne F, is described. (3SR,5SR,6SR)-6-Ethyltetrahydro-3,5-dimethyl-2H-pyran-2-one (10) is prepared in 65percent yield through lactonization of a 1:1 mixture of C-2 epimrs of the corresponding esters.
A new synthesis of serricornin [(4s,6s,7s)-7-hydroxy-4,6-dimethyl-3-nonanone], the sex pheromone of the cigarette beetle
Mori, Kenji,Watanabe, Hidenori
, p. 3423 - 3428 (2007/10/02)
Serricornin, the sex pheromone of Lasioderma serricorne F, was synthesised in 7.6% overall yield starting from methyl (R)-3-hydroxypentanoate of microbial origin. Its (4R,6S,7S)-isomer was also synthesised.
ELECTROPHILIC LACTONIZATION AS A TOOL IN ACYCLIC STEREOCONTROL; SYNTHESIS OF SERRICORNIN
Bartlett, Paul A.,Richardson, David P.,Myerson, Joel
, p. 2317 - 2327 (2007/10/02)
Several electrophilic lactonization procedures have been explored as a means of functionalizing olefinic carboxylic acids with relative asymmetric induction.Iodolactonization of δ,ε-unsaturated acids under conditions of thermodynamic control exhibits good
Stereoselective Synthesis of Alcohols, XVIII. - Synthesis of (3S,4S)-4-Methyl-3-heptanol and of (5S,6S)-Anhydroserricornin
Hoffmann, Reinhard W.,Ladner, Wolfgang,Helbig, Wilfried
, p. 1170 - 1179 (2007/10/02)
Yeast reduction of methyl tetrahydro-4-oxo-2H-thiopyran-3-carboxylate (5) led to the β-hydroxy ester 6 of 98percent diastereomeric and ca. 85percent enantiomeric purity. 6 was converted into enantiomerically pure anti-4-methyl-3-heptanol (4) and via the key intermediate 11 into enantiomerically pure anhydroserricornin (3).
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
