Two Total Syntheses of Showdomycin and Related Studies

Anthony G.M. Barrett, Howard B. Broughton, Steven V. Attwood, Leslie Gunatilaka

Research output: Contribution to journalArticle

54 Scopus citations

Abstract

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).

Original languageEnglish (US)
Pages (from-to)495-503
Number of pages9
JournalJournal of Organic Chemistry
Volume51
Issue number4
DOIs
StatePublished - Feb 1 1986
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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