128303-13-9Relevant academic research and scientific papers
A facile access to pyrroles from amino acids via an aza-Wacker cyclization
Zhang, Zuhui,Zhang, Jintang,Tan, Jiajing,Wang, Zhiyong
, p. 5180 - 5182 (2008/12/20)
(Chemical Equation Presented) A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf) 2. A series of pyrroles were obtained by this method under mild conditions.
Synthesis and field bioassay of the Israeli pine bast scale, Matsucoccus josephi, female sex pheromone
Zegelman, Lev,Hassner, Alfred,Mendel, Zvi,Dunkelblum, Ezra
, p. 5641 - 5644 (2007/10/02)
We report the first synthesis of the two components of the female sex pheromone of Matsucoccus josephi (2E,4E,8E)-4,6-dimethyl-2,4,8-decatrien-7-one (1) and (2E,4Z,8E)-4,6-dimethyl-2,4,8-decatrien-7-one (2) utilizing the Reformatzky and Wittig reactions as key steps. A mixture of 1 and 2 and the separate isomers were bioassayed in a pine forest indicating that E isomer 1 is much more active than 2 and is also a kairomone for a predator.
Acyclic Stereocontrol through the Thio-Claisen Rearrangement of Precursors bearing a Chiral Centre adjacent to Carbon 1
Desert, Stephane,Metzner, Patrick,Ramdani, Mohamed
, p. 10315 - 10326 (2007/10/02)
The Claisen rearrangement of precursors bearing a stereogenic centre adjacent to carbon 1 of the pericyclic nucleus has been investigated in the sulfur series.Dithioesters having a methyl and various alkyl or alkenyls groups on the β-carbon were deprotonated by LDA.The resulting enethiolates were allylated on sulfur to give S-allyl ketenedithioacetals.The thio-Claisen transposition of the latter compounds was achieved either at room temperature or at 101 deg C to afford good yield of allylated dithioesters.Diastereomeric selectivities up to 95:5 have been observed.These results have been explained by a steric effect and correlated to allylic strain values.
