88376-72-1Relevant academic research and scientific papers
Enantioselective synthesis of chiral β-aryloxy alcohols by asymmetric hydrogenation of a-aryloxy aldehydes via dynamic kinetic resolution
Zhou, Zhang-Tao,Xie, Jian-Hua,Zhou, Qi-Lin
body text, p. 363 - 366 (2009/11/30)
A catalytic enantioselective hydrogenation of racemic α-aryloxy aldehydes via dynamic kinetic resolution has been developed by using (diamine)(spirodiphosphine)ruthenium(II) chloride [RuCl 2(SDPs)(diamine)] catalysts. Employing this new reactio
On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae
Schweifer, Anna,Hammerschmidt, Friedrich
, p. 3056 - 3059 (2008/12/23)
2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 μg/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%) in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin.
Convergent approach to pumiliotoxin alkaloids. Asymmetric total synthesis of (+)-pumiliotoxins A, B, and 225F
Aoyagi, Sakae,Hirashima, Shintaro,Saito, Kosuke,Kibayashi, Chihiro
, p. 5517 - 5526 (2007/10/03)
A versatile convergent approach for preparing the pumiliotoxin alkaloids has been developed employing Pd(0)-catalyzed cross-coupling reactions between homoallylic organozincs and vinyl iodides. The (Z)-iodoalkylidene indolizidine 34, which served as a common key intermediate, was synthesized through highly stereoselective addition of the chiral silylallene 19 to (S)-acetylpyrrolidine followed by a palladium-catalyzed intramolecular carbonylation-cyclization sequence. This synthetic process allowed the first total synthesis of (+)-pumiliotoxin 225F. The intermediate (Z)-iodoalkylidene indolizidine 34 obtained was converted to a homoallylzinc chloride derivative and subjected to homoallyl-vinyl cross-coupling with the (E)-vinyl iodide 42 using Pd(PPh3)4 catalyst to give the cross-coupled product 47 with a 1,5-diene side chain. Subsequent deprotection provided (+)-pumiliotoxin A. On the other hand, the (Z)-iodoalkylidene indolizidine 34 was transformed into the homoallyl-tert-butyl zinc derivative, which underwent palladium-catalyzed cross-coupling with the (E)-vinyl iodide 50 and subsequent deprotection to afford (+)-pumiliotoxin B.
Enantio- and Diastereocontrolled Synthesis of Chiral 1,2-Diol Derivatives from (R)-2,3-Di-O-isopropylideneglyceraldehyde: endo- and exo-Brevicomin
Mulzer, Johann,Angermann, Alfred,Muench, Winfried
, p. 825 - 838 (2007/10/02)
All four possible stereoisomers of the insect pheromone brevicomin have been prepared from (R)-2,3-di-O-isopropylideneglyceraldehyde (1) on stereocontrolled routes with ee more than 98-99percent.
AN ASYMMETRIC SYNTHESIS OF α-BENZYLOXY ALDEHYDES HAVING A CHIRAL TERTIARY CENTER - AN APPLICATION TO THE ASYMMETRIC SYNTHESIS OF exo-(+)-BREVICOMIN -
Asami, Masatoshi,Mukaiyama, Teruaki
, p. 93 - 96 (2007/10/02)
α-benzyloxy aldehydes having a chiral tertiary center at α-carbon atom are synthesized in high enantiomeric excess by successive treatment of 2-methoxycarbonyl-3-phenyl-1,3-diazabicyclooctane with diisobutylaluminum hydride (DIBAL-H) and Grignard reagents.The asymmetric reaction is applied to the total synthesis of exo-(+)-brevicomin.
