Synthesis of Sinefungin and Its C-6' Epimer

Article abstract of DOI:10.1021/ja00364a028

A synthesis of the nucleoside antibiotic sinefungin (1) and its C-6' epimer is described.It was accomplished by coupling a functionized adenosine derivative, 2, with an aldehyde synthon, 3, derived from L-amino acid to give the sinefungin precursor 4.The construction of the skeleton of the glycosyl moiety of sinefungin (1) could be achieved starting from methyl riboside.The adopted sequence was probed further by synthesizing the sinefungin analogue 9b (two C-6' epimers).This synthesis established that the Hoffmann rearrangement of both amides 8b took place with complete retention of configuration at C-6'.Finally, sinefungin derivatives 9c were obtained, and one of these found to be identical with the same derivative prepared from authentic sinefungin (1).It was easily converted to sinefungin (1).