6064-52-4Relevant articles and documents
Microbial bioreductions of γ- and δ-ketoacids and their esters
Forzato, Cristina,Gandolfi, Raffaella,Molinari, Francesco,Nitti, Patrizia,Pitacco, Giuliana,Valentin, Ennio
, p. 1039 - 1046 (2007/10/03)
A series of yeasts were used in the bioreductions of aliphatic and aromatic γ- and δ-ketoacids and esters to investigate the preparation of enantiomerically pure γ- and δ-lactones through the intermediacy of their corresponding γ- and δ-hydroxyacids and esters. Bioreduction of ethyl 4-oxononanoate 2a with Pichia etchellsii afforded the γ-nonanolide (+)-5a with 99% e.e., while Pichia minuta proved to be the best choice for the bioreduction of ethyl 2-oxocyclohexylacetate 2e, which afforded cis-(-)-5e and trans-(-)-5e with 98 and 99% e.e., respectively. Reduction of 3-(2-oxocyclohexyl)propionic acid 3e with Pichia glucozyma gave predominantly the corresponding δ-lactone trans-(-)-6e with 94% e.e., whose absolute configuration was determined by means of CD spectroscopy.
A CONVENIENT METHOD FOR THE SYNTHESIS OF 4-CHLORO-3-ALKENOIC ACID, A NEW USEFUL SYNTHETIC BLOCK FOR 4-OXOALKANOIC AND 4-OXO-2-ALKENOIC ACIDS
Kawashima, Masatoshi,Fujisawa, Tamotsu
, p. 1851 - 1854 (2007/10/02)
Easily available material, β-(1-chlorovinyl)-β-propiolactone reacted with organocopper reagents to afford 4-chloro-3-alkenoic acids in high yields.The acids were easily transformed into two kinds of useful carboxylic acids such as 4-oxoalkanoic and 4-oxo-(E)-2-alkenoic acids leading to various natural products.