TY - JOUR
T1 - A chemo-enzymatic expeditious route to racemic dihexanoyl (2R*,3R*,4R*)-dehydroxymethylepoxyquinomycin (DHMEQ), the precursor for lipase-catalyzed synthesis of the potent nuclear factor-κB inhibitor, (2 S,3S,4 S )-DHMEQ
AU - Kobayashi, Ryohei
AU - Hanaya, Kengo
AU - Shoji, Mitsuru
AU - Umezawa, Kazuo
AU - Sugai, Takeshi
PY - 2012/9
Y1 - 2012/9
N2 - In order to synthesize the potent nuclear factor (NF)- κB inhibitor, (2S ,3 S ,4 S )-dehydroxymethylepoxyquinomycin (DHMEQ), in a large scale, a new route for its corresponding racemic precursor, dihexanoyl (2R*,3R*, 4R*)- DHMEQ, was developed. By employing both hydroquinone and benzoquinone intermediates, the total yield, reproducibility, and synthetic steps were improved and the synthetic cost was reduced.
AB - In order to synthesize the potent nuclear factor (NF)- κB inhibitor, (2S ,3 S ,4 S )-dehydroxymethylepoxyquinomycin (DHMEQ), in a large scale, a new route for its corresponding racemic precursor, dihexanoyl (2R*,3R*, 4R*)- DHMEQ, was developed. By employing both hydroquinone and benzoquinone intermediates, the total yield, reproducibility, and synthetic steps were improved and the synthetic cost was reduced.
KW - Benzoquinone
KW - Dehydroxymethylepoxyquinomycin
KW - Epoxidation
KW - Hydroquinone
KW - Oxidation
KW - Process chemistry
UR - http://www.scopus.com/inward/record.url?scp=84865959777&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84865959777&partnerID=8YFLogxK
U2 - 10.1248/cpb.c12-00417
DO - 10.1248/cpb.c12-00417
M3 - Article
C2 - 22976334
AN - SCOPUS:84865959777
SN - 0009-2363
VL - 60
SP - 1220
EP - 1223
JO - Chemical and Pharmaceutical Bulletin
JF - Chemical and Pharmaceutical Bulletin
IS - 9
ER -