97776-79-9Relevant academic research and scientific papers
STEREOCONTROLLED SYNTHESIS OF A C14-C20 BUILDING BLOCK FOR AMPHOTERICIN B USING A NOVEL WITTIG REARRANGEMENT
Bruecker, Reinhard
, p. 5747 - 5750 (2007/10/02)
The C14-C20 unit 11 of the polyene macrolide antibiotic amphotericin B (1) was synthesized from L-arabinose in 13 steps.The key step 7 -> 10 features diastereocontrol through asymmetric induction in a novel Wittig rearrangement.
A Convenient Synthesis of Four Stereoisomers of 6-Acetoxy-5-hexadecanolide, the Major Component of the Mosquito Oviposition Attractant Pheromone
Machiya, Kozo,Ichimoto,Itsuo,Kirihata, Mitsunori,Ueda, Hiroo
, p. 643 - 650 (2007/10/02)
The major component of the mosquito oviposition attractant pheromone (5S,6R)-(+)- and (5R,6S)-(-)-erythro-6-acetoxy-5-hexadecanolide and their threo-isomers, (5R,6R)-(+)- and (5S,6S)-(-)-6-acetoxy-5-hexadecanolide were synthesized from isopropylidene-D-glyceraldehyde and isopropylidene-L-glyceraldehyde, respectively, in which the nucleophilic addition of Grignard reagent involved the diastereoface-differentiating process as the key step.The bioassay of four erythro- and threo-isomers against mosquito (Culex pipiens molestus) was conducted. (5R,6S)-(-)-erythro-6-acetoxy-5-hexadecanolide proved to be the most effective as an attractant.
