
%0 Journal Article
%A Brimble, Margaret A. 
%A Robinson, James E. 
%A Choi, Ka Wai 
%A Woodgate, Paul D. 
%T Synthesis of a Novel Nucleoside Based on a Spiroacetal Framework
%J Australian Journal of Chemistry
%D 2004/07/07
%V 57
%N 7
%P 665-668
%K 
%R https://doi.org/10.1071/CH04021
%U https://www.publish.csiro.au/paper/CH04021 
%X The first synthesis of a nucleoside analogue 1 is reported wherein the nucleobase 5-fluorocytosine is attached to a 1,6-dioxaspiro[5.5]undecane spiroacetal ring system. The spiroacetal system acts as a substitute for the sugar unit of natural nucleosides and provides a conformationally restricted framework upon which to append nucleobases in a well defined geometry. Trimethylsilyl triflate promoted Vorbr&#252;ggen-type coupling of bis(trimethylsilyl)-5-fluorocytosine 3 with spiroacetal acetate 2 provided spiroacetal nucleoside 1 in which the nucleobase occupied an equatorial position together with the ring opened (Z)-alkene 10. Spiroacetal acetate 2 serves as the spiroacetal donor and was prepared from the readily available starting materials &#948;-valerolactone and but-3-yn-1-ol 4. 
