
TY  - JOUR
A1  - Brimble, Margaret A. 
A1  - Robinson, James E. 
A1  - Choi, Ka Wai 
A1  - Woodgate, Paul D. 
T1  - Synthesis of a Novel Nucleoside Based on a Spiroacetal Framework
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2004
VL  - 57
IS  - 7
SP  - 665
EP  - 668
KW  - 
UR  - https://doi.org/10.1071/CH04021 
N2  - 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. 
ER  -

