4395-37-3Relevant academic research and scientific papers
SYNTHETIC STUDIES ON BIOLOGICALLY ACTIVE NATURAL PRODUCTS BY A CHEMICOENZYMATIC APPROACH. ENANTIOSELECTIVE SYNTHESIS OF C- AND N-NUCLEOSIDES, SHOWDOMYCIN, 6-AZAPSEUDOURIDINE AND CORDYCEPIN
Ohno, Masaji,Ito, Yukishige,Arita, Masafumi,Shibata, Tomoyuki,Adachi, Kunitomo,Sawai, Hiroaki
, p. 145 - 152 (2007/10/02)
An efficient synthesis of C- and N-nucleosides has been developed in an enantioselective and stereocontrolled manner starting from Diels-Alder adduct of furan and dimethyl acetylenedicarboxylate by chemicoenzymatic strategy.The symmetric unsaturated dimethyl esters 2 and 3 were almost quantitatively hydrolysed with pig liver esterase to yield half-esters 4 and 5 with reasonably high optical yields.Decarboxylative ozonolysis of the chiral half-esters 4 followed by chemical transformation afforded methyl-L-riboside 12, but after the enantiomer conversion (4 to 13 and 5 to 28) the methyl D-riboside (17), (+)-showdomycin (22), and (-)-6-azapseudouridine (27), were obtained from 13, and (-)-cordycepin (32) was obtained from 28.
