150408-28-9Relevant articles and documents
Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals
Kumari, Anupama,Gholap, Sachin P.,Fernandes, Rodney A.
, p. 2278 - 2290 (2019)
A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.
Blue fluorescence generated during lipid oxidation of rat liver microsomes cannot be derived from malonaldehyde but can be from other aldehyde species
Inoue, Tadamichi,Kikugawa, Kiyomi
, p. 319 - 325 (1998)
Generation of blue fluorescence together with phospholipid hydroperoxides and aldehyde species in rat liver microsomes during oxidation with FeCl2-ADP-ascorbic acid was monitored, and the kind of lipid oxidation products participating in the formation of blue fluorescence was investigated. Contents of phospholipid hydroperoxides were increased in an early stage of oxidation, and were decreased in an advanced stage of oxidation. Contents of components that liberated malonaldehyde, 4- hydroxyalkenals and other unsaturated aldehydes under the acidic assay conditions were increased in the advanced stage of oxidation. Water-soluble blue fluorescence with a maximum at 440-450 nm determined after separation through gel filtration accumulated in the advanced stage of oxidation, and was characterized as resistant to borohydride treatment and to be little dependent on pH values of the solvent. Wavelength of the maximum fluorescence and characteristics of the fluorescence were similar to those of fluorescence with maxima at 440-450 nm formed by reaction of unoxidized microsomes, bovine serum albumin or methylamine with alkenals, and different from those of fluorescence with maxima at above 460 nm obtained by the reaction with a mixture containing malonaldehyde. Hence, blue fluorescence accumulated in oxidized microsomes cannot be derived from free malonaldehyde but can be from other aldehyde species including alkenals.
Natural (5′-oxoheptene-1′E,3′E-dienyl)-5,6-dihydro-2H- pyran-2-one: Total synthesis and revision of its absolute configuration
Bouzbouz, Samir,De Lemos, Elsa,Cossy, Janine,Saez, Jairo,Franck, Xavier,Figadère, Bruno
, p. 2615 - 2617 (2007/10/03)
The synthesis of (5′-oxoheptene-1′E,3′E-dienyl)-5,6- dihydro-2H-pyran-2-one has been performed in seven steps using four key steps: a ring-closing metathesis reaction to build up the unsaturated lactone, a Wittig reaction to control the C6-C7 (E) double bond, a cross-metathesis reaction to control the (E) double bond at C8-C9, and an enantioselective allyltitanation to control the absolute configuration at C5. Spectroscopic data (IR, MS, 1H, and 13C NMR) were identical to those of the natural compound except for the optical rotation, which led us to re-assign the absolute configuration of the natural product.
