Journal of Organic Chemistry p. 495 - 503 (1986)
Update date:2022-09-26
Topics:
Barrett, Anthony G. M.
Broughton, Howard B.
Attwood, Steven V.
Gunatilaka, A. A. Leslie
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).
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