Two Total Syntheses of Showdomycin and Related Studies

Article abstract of DOI:10.1021/jo00354a017

After a series of model reactions, D-ribose (2) was reacted with 3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8a) in THF at reflux to produce 3(E)-2(S),3(S),4(R),5-tetrahydroxy-1-pentylidene)-2,5-pyrrolidinedione (35) (75 percent).Subsequent cyclization of 35 using phenylselenyl chloride followed by hydrogen peroxide gave showdomycin (1) (13 percent) and epi-showdomycin (36) (41 percent).Using a similar strategy 2,3-O-isopropylidene-D-ribose (37b) was reacted sequentially with 1-(triphenylmethyl)-3-(triphenylphosphoranylidene)-2,5-pyrrolidinedione (8b), phenylselenyl chloride, hydrogen peroxide, and trifluoroacetic acid to give (1) (3 percent overall).