TY - JOUR
T1 - Two Total Syntheses of Showdomycin and Related Studies
AU - Barrett, Anthony G.M.
AU - Broughton, Howard B.
AU - Attwood, Steven V.
AU - Gunatilaka, Leslie
PY - 1986/2/1
Y1 - 1986/2/1
N2 - 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%). Subsequent cyclization of 35 using phenylselenenyl chloride followed by hydrogen peroxide gave showdomycin (1) (13%) and epi-showdomycin (36) (41%). Using a similar strategy 2, 3-O-iso-propylidene-D-ribose (37b) was reacted sequentially with 1-(triphenylmethyl)-3-(triphenylphosphoranylidene)-2, 5-pyrrolidinedione (8b), phenylselenenyl chloride, hydrogen peroxide, and trifluoroacetic acid to give 1 (3% overall).
AB - 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%). Subsequent cyclization of 35 using phenylselenenyl chloride followed by hydrogen peroxide gave showdomycin (1) (13%) and epi-showdomycin (36) (41%). Using a similar strategy 2, 3-O-iso-propylidene-D-ribose (37b) was reacted sequentially with 1-(triphenylmethyl)-3-(triphenylphosphoranylidene)-2, 5-pyrrolidinedione (8b), phenylselenenyl chloride, hydrogen peroxide, and trifluoroacetic acid to give 1 (3% overall).
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U2 - 10.1021/jo00354a017
DO - 10.1021/jo00354a017
M3 - Article
AN - SCOPUS:0022633765
SN - 0022-3263
VL - 51
SP - 495
EP - 503
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -