153259-38-2Relevant academic research and scientific papers
Two Enantioselective Syntheses of the Diol Precursor of the Biologically Most Active Isomer of an Insect Growth Regulator
Buser, Hans-Peter,Spindler, Felix
, p. 2451 - 2460 (2007/10/02)
The diol precursor (R)-3 of the insect growth regulator 2 was synthesized enantioselectively by two different routes: a) via enantioselective hydrogenation of the α-hydroxy-ketone 4, catalyzed by Ru-BINAP-catalyst and b) via resolution of the enantiomers of glycerol using (-)-camphor-10-sulfonamide 7 as chiral auxiliary.
Insect Juvenile Hormone Mimics: A Chemical Metamorphosis from Terpenoid Esters to Aryloxy-Dioxolanes
Karrer, Friedrich,Kayser, Hartmut,Buser, Hans Peter,Tombo, Gerardo M. Ramos
, p. 302 - 306 (2007/10/02)
The 1,3-dioxolane derivative 5 is a potent juvenile hormone mimic.The stereoselective synthesis of its stereoisomers 6-9 was based on the chiral glycerol derivative 12.Three different approaches to this central compound 12 were investigated: using chiral building blocks, enantioselective catalytic hydrogenation, and stereoselective crystallization.The latter is the most suitable for large scale synthesis.In vivo testing of the different stereoisomers on Nauphoeta cinerea showed that the juvenoid activity is mainly associated with the (2R,4S)-6 isomer.
