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

53 Citations (Scopus)

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-isopropylidene-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
StatePublished - 1986
Externally publishedYes

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Showdomycin
Succinimides
Ribose
Hydrogen Peroxide
Trifluoroacetic Acid
Cyclization

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Barrett, A. G. M., Broughton, H. B., Attwood, S. V., & Gunatilaka, L. (1986). Two total syntheses of showdomycin and related studies. Journal of Organic Chemistry, 51(4), 495-503.

Two total syntheses of showdomycin and related studies. / Barrett, Anthony G M; Broughton, Howard B.; Attwood, Steven V.; Gunatilaka, Leslie.

In: Journal of Organic Chemistry, Vol. 51, No. 4, 1986, p. 495-503.

Research output: Contribution to journalArticle

Barrett, AGM, Broughton, HB, Attwood, SV & Gunatilaka, L 1986, 'Two total syntheses of showdomycin and related studies', Journal of Organic Chemistry, vol. 51, no. 4, pp. 495-503.
Barrett, Anthony G M ; Broughton, Howard B. ; Attwood, Steven V. ; Gunatilaka, Leslie. / Two total syntheses of showdomycin and related studies. In: Journal of Organic Chemistry. 1986 ; Vol. 51, No. 4. pp. 495-503.
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