The metathesis reaction for side chain construction in carbocyclic sinefungin analogue synthesis

The naturally occurring nucleoside sinefungin has found considerable use in biological investigations. More extensive sinefungin studies have been limited because few analogues have been reported due to the synthetic challenges associated with such studies. Reported herein are preparative ways to two carbocyclic sinefungin analogues: 6′-deaminocarbocyclic sinefungin and (S)-6′-hydroxy-6′-deaminocarbocyclic sinefungin. The synthetic routes were made efficient and practical by the application of two metathesis reactions employing second generation Grubbs catalyst.