Two total syntheses of showdomycin and related studies

AGM Barrett, HB Broughton, SV Attwood…

Index: Barrett, Anthony G. M.; Broughton, Howard B.; Attwood, Steven V.; Gunatilaka, A. A. Leslie Journal of Organic Chemistry, 1986 , vol. 51, # 4 p. 495 - 503

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Citation Number: 55

Abstract

After a series of model reactions, D-ribose (2) was reacted with 3-( triphenylphosphoranylidene)-2, 5-pyrrolidinedione (sa) in THF at reflux to produce 3 (E)-(2 (S), 3 (S), 4 (R), 5-tetrahydroxy-l-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- ...