139911-66-3Relevant academic research and scientific papers
Proto- and iodo-lactonization reaction of substituted α,β: γ,δ- unsaturated carboxylic acid
Kuroda, Chiaki,Tang, Chen Ying,Tanabe, Makoto,Funakoshi, Masabumi
, p. 1583 - 1587 (1999)
Iodolactonization of 4,5-disubstituted 2-(trimethylsilylmethyl)- and 2- methyl-penta-2,4-dienoic acids was studied. The latter afforded the corresponding iodolactone in good yield by treatment with I2 in MeCN. Iodolactone was also obtained by treatment with I2/NaHCO3/CHCl3/H2O in the presence of cerium(IV) salt as an additive. It was found that protolactonization proceeds by the aid of the trimethylsilyl group, while it prevents iodolactonization.
Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-[(E)-cycloalk-2-enylidenemethyl] thiolactomycin congeners
Ohata, Kohei,Terashima, Shiro
experimental part, p. 920 - 936 (2010/03/23)
The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure-activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2- enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.
Synthesis and biological activity of enantiomeric pairs of 5-[(E)-cycloalk-2-enylidenemethyl]thiolactomycin congeners
Ohata, Kohei,Terashima, Shiro
scheme or table, p. 5598 - 5600 (2009/05/30)
The title congeners were synthesized by employing our efficient synthetic route previously explored for preparing enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. While all the synthesized congeners lacked in vitro antibacterial activit
New C-C bond formation through the nickel-catalysed electrochemical coupling of 1,3-enynes and carbon dioxide
Derien, Sylvie,Clinet, Jean-Claude,Dunach, Elisabet,Perichon, Jacques
, p. 213 - 224 (2007/10/02)
A series of 1,3-enynes has been carboxylated in a nickel-catalysed electrochemical reaction carried out in a single-compartment cell fitted with a consumable magnesium anode.When 2,2'-bipyridine (bipy) or pentamethyldiethylene triamine (PMDTA) are added a
