67 新規ヌクレオシド、オキセタノシンの合成及びオキセタノースの化学(ポスター発表の部)

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Oxetanocin, a novel nucleoside antibiotic carrying a oxetanose as a sugar moiety, has exhibited remarkable antiviral activities. This intriguing antibiotic prompted us to start synthetic studies including related compounds as well as a new oxetanose chemistry, which are ultimately focused on developments of efficient antiviral agents deeming 1 a lead compound. In this presentation we disclose our recent research process. Conversion of the base moiety of 1 into uracil was attempted to elucidate a structure-activity relationship. Upon treatment of acylated oxetanocin (2) with silyluracil derivative in the presence of SnCl_4, the product was not an expected oxetanosyl glycoside, but L-threofuranosyl derivative (3,4) via an unusual ring expansion process. Application of this reaction could provide the corresponding C-glycoside (5). Total synthesis of oxetanocin (1) could be accomplished. During this research, novel oxetanoses was obtained as 1-O-acyl derivative by Baeyer-Villiger oxidation of the corresponding oxetane. On the basis of deprotection of 6 involving a seven-membered ring participation, successful glycosidation reaction of 7 to 1 could be performed. A facile synthetic method of oxetanoses was developed by a basic ring closure of epoxy alcohols as a key step, in which a cis epoxide afforded selectively an oxetane derivative (10), whereas a trans one yielded a tetrahydrofuran (11). Differences of these reactions would be discussed by AM1 calculations. Epinor-oxetanocin has been known to have more potent antiviral activities than 1. Related noroxetanocin has also been synthesized using Fleet's method.
天然有機化合物討論会の論文
1990-09-25

67 新規ヌクレオシド、オキセタノシンの合成及びオキセタノースの化学(ポスター発表の部)

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