626-88-0Relevant articles and documents
A short synthesis of (Z)-15-methylhexadec-11-enoic acid
Reyes, Elba D.,Carballeira, Néstor M.
, p. 693 - 694 (1996)
The biologically intriguing (Z)-15-methylhexadec-11-enoic acid, a component of Myxococcus xanthus and Cyamopsis tetragonolobus, has been synthesized in 19% overall yield via the Wittig reaction of 4-methyl-1-pentyltriphenylphosphonium bromide and 10-bromodecanal. The title compound displayed marginal cytotoxicity against human cervix carcinoma (HeLa) and Chinese hamster ovary (CHO) cells.
Synthesis of disparlure analogues, using resolution on microcrystalline cellulose triacetate-I
Inkster, James A. H.,Ling, Ivy,Honson, Nicolette S.,Jacquet, Loic,Gries, Regine,Plettner, Erika
, p. 3773 - 3784 (2007/10/03)
The gypsy moth, Lymantria dispar, uses a chiral epoxide, (+)-(7R,8S)-2-methyl-7,8-epoxyoctadecane, (+)-disparlure, as its main sex attractant. The moths can detect both enantiomers of disparlure and respond differently to each one. In an effort to understand the structure-activity relationships of the gypsy moth olfactory system, we prepared the analogues of (+)- and (-)-disparlure. The key intermediate in route to the analogues was 2-epoxytridecan-1-ol. Herein we report the resolution of 2-epoxytridecan-1-yl esters on microcrystalline cellulose triacetate and the synthesis of 5-oxa and (5Z)-ene analogues of (+)- and (-)-disparlure. An effort to make 5-aza analogues resulted in the formation of anti-5-(1-hydroxy-1-undecyl)-3-(3-methylbutyl) oxazolidin-2-one. The analogues were tested for their electroantennogram responses and for their ability to bind to pheromone-binding protein 1 (PBP1). We found that the 5-oxa analogues gave strong responses and that the antenna and the PBP1 no longer distinguish the enantiomers of the 5-oxa analogues. The analogues all bound the PBP1 with similar affinity to (-)-disparlure.
Asymmetric synthesis of A-factor
Crawforth, James M.,Fawcett, John,Rawlings, Bernard J.
, p. 1721 - 1725 (2007/10/03)
The synthesis of enantlopure A-factor ['autoregulatory factor'; (3R)-(-)-2-(6-methylheptanoyl)-3-hydroxymethylbutano-4-lactone] by the completely diastereoselective benzyloxymethylation of (4R)-3-(3-phenylpropanoyl)-4-isopropyloxazolidin-2-one is reported.