130607-25-9Relevant academic research and scientific papers
One-step synthesis of (-)-5-epi-hydantocidin
Nakajima, Noriyuki,Kirihara, Masayuki,Matsumoto, Miyoko,Hashimoto, Masaru,Katoh, Tadashi,Terashima, Shiro
, p. 503 - 508 (2007/10/03)
One-step synthesis of (-)-5-epi-hydantocidin was achieved by heating a mixture of D-isoascorbic acid and urea without solvent. Studies on N,O-spiroketal formation and epimerization between (+)-hydantocidin and (-)-5-epi-hydantocidin were also carried out to explore some mechanistic aspects of the obtained results.
Novel synthesis of (+)-hydantocidin based on the plausible biosynthetic pathway
Nakajima, Noriyuki,Matsumoto, Miyoko,Kirihara, Masayuki,Hashimoto, Masaru,Katoh, Tadashi,Terashima, Shiro
, p. 1177 - 1194 (2007/10/03)
The title synthesis was examined by employing two synthetic schemes which feature N,O-spiroketal formation as a key step. Although the stepwise synthesis starting with D-fructose and proceeding through the D-psicose derivatives successfully produced a mixture of (+)-hydantocidin (1) and its C5-epimer [(-)-5-epihydantocidin (2)], the one-step synthesis utilizing D-isoascorbic acid and urea as starting materials was found to give 2 more selectively than 1. Studies on the key N,O-spiroketal formation and epimerization between 1 and 2 were also carried out to explore some novel aspects of the obtained results.
Stereoselective bromination of β-ribofuranosyl amide. Enantioselective synthesis of (+)-hydantocidin
Harrington,Harrington, Philip M.,Jung,Jung, Michael E.
, p. 5145 - 5148 (2007/10/02)
The synthesis of hydantocidin, a potent herbicidal natural product, is highlighted by a stereoselective bromination of β-D-ribofuranosyl amide to give only the α-bromo β-amide and subsequent spirocyclization about the anomeric position with silver cyanate to form the hydantoin moiety.
A novel biogenetic type synthesis of (+)-hydantocidin
Matsumoto, Miyoko,Kirihara, Masayuki,Yoshino, Toshiharu,Katoh, Tadashi,Terashima, Shiro
, p. 6289 - 6292 (2007/10/02)
The title synthesis was accomplished by featuring the proposed biosynthetic pathway. The synthesis commenced with the D-psicose derivative readily obtainable from D-fructose and employed intramolecular N, O-spiroketal formation of the open-chain N-acylurea derivative as a key step.
