1330745-75-9Relevant academic research and scientific papers
Access to oxetane-containing psico-nucleosides from 2-methyleneoxetanes: A role for neighboring group participation?
Liang, Yanke,Hnatiuk, Nathan,Rowley, John M.,Whiting, Bryan T.,Coates, Geoffrey W.,Rablen, Paul R.,Morton, Martha,Howell, Amy R.
, p. 9962 - 9974 (2012/02/05)
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 assistance to increase the selectivity was not fruitful. A range of 2-methyleneoxetane and related 2-methylenetetrahydrofuran substrates was prepared to explore the basis for this. With one exception, these substrates also showed little stereoselectivity in nucleobase incorporation. Computational studies were undertaken to examine if neighboring group participation involving fused [4.2.0] or [4.3.0] intermediates is favorable (Figure presented).
Silver-mediated exo-selective tandem desilylative bromination/ oxycyclization of silyl-protected alkynes: Synthesis of 2-bromomethylene- tetrahydrofuran
Lee, Hyun-Ji,Lim, Chaemin,Hwang, Soonho,Jeong, Byeong-Seon,Kim, Sanghee
supporting information; experimental part, p. 1943 - 1947 (2011/11/30)
Three in one: The exocyclic β-bromo enol ether is a synthetically useful functional moiety in the preparation of functionalized oxygen heterocycles. A new tandem method for the synthesis of this valuable moiety has been achieved by employing silyl-protect
