Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: a role for neighboring group participation?

…, N Hnatiuk, JM Rowley, BT Whiting…

文献索引：Liang, Yanke; Hnatiuk, Nathan; Rowley, John M.; Whiting, Bryan T.; Coates, Geoffrey W.; Rablen, Paul R.; Morton, Martha; Howell, Amy R. Journal of Organic Chemistry, 2011 , vol. 76, # 24 p. 9962 - 9974

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被引用次数: 18

摘要

The first psico-oxetanocin analogue of the powerful antiviral natural product, oxetanocin A, has been readily synthesized from cis-2-butene-1, 4-diol. Key 2-methyleneoxetane precursors were derived from β-lactones prepared by the carbonylation of epoxides. F+- mediated nucleobase incorporation provided the corresponding nucleosides in good yield but with low diastereoselectivity. Surprisingly, attempted exploitation of anchimeric ...