82079-32-1Relevant articles and documents
Variable synthesis of the optically active thiotetronic acid antibiotics thiolactomycin, thiotetromycin, and 834-B1
Dormann, Korinna L.,Brueckner, Reinhard
, p. 1160 - 1163 (2007)
(Chemical Equation Presented) In seven steps: The antibiotic (+)-thiolactomycin was synthesized in seven steps and with 16% overall yield from 4-acetoxy-2-methyl-2-buten-1-al, an intermediate of the industrial synthesis of vitamin A. Key transformations were the catalytic asymmetric Sharpless epoxidation of an ethoxycarbonyl-substituted pentadienol (93% ee) and a regio- and stereoselective thiolysis of the resulting epoxide (see scheme).
Lipase-catalyzed kinetic resolution of thiotetronic acid derivatives bearing a chiral quaternary carbon: total synthesis of (R)-thiolactomycin and its O-analogue
Toyama, Ken-ichi,Tauchi, Tetsuo,Mase, Nobuyuki,Yoda, Hidemi,Takabe, Kunihiko
, p. 7163 - 7166 (2006)
We have developed a chemoenzymatic synthesis of (R)-thiolactomycin (1) having a chiral quaternary carbon atom at C5. In the kinetic resolution of the thiotetronic acid precursor 4, both enantiomers were obtained with high enantiomeric excess by use of Chirazyme L-2. Chemical transformations of the (R)-alcohol 4 provided the chiral (R)-thiolactomycin (1) in 36% yield in five steps.
Efficient synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative
Ohata, Kohei,Terashima, Shiro
, p. 2787 - 2791 (2007/10/03)
Starting with commercially available tiglic aldehyde, the title synthesis was achieved by employing deconjugative asymmetric α-sulfenylation of the chiral 3-(α,β,γ,δ-unsaturated acyl)-2-oxazolidinone with a methanethiosulfonate as a key step.
