Practical total synthesis of fuligocandins A and B

Midori A. Arai, Junya Seto, Firoj Ahmed, Kento Uchiyama, Masami Ishibashi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fuligocandins A and B, cycloanthranilylproline derivatives isolated from the myxomycete Fuligo candida, were synthesized efficiently by a Meyer-Schuster rearrangement, which gave Z-isomer with high selectivity. The absolute stereochemistry at C-11a of the natural products was determined to be S by comparison of the optical rotation of the natural products with synthetic counterparts derived from l-proline. This report is the first total synthesis of optically active fuligocandin B.

Original languageEnglish
Pages (from-to)2498-2502
Number of pages5
JournalSynlett
Issue number16
DOIs
Publication statusPublished - 2010 Sep 30
Externally publishedYes

Keywords

  • fuligocandin
  • Meyer-Schuster rearrangement
  • myxomycete
  • total synthesis
  • TRAIL

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Arai, M. A., Seto, J., Ahmed, F., Uchiyama, K., & Ishibashi, M. (2010). Practical total synthesis of fuligocandins A and B. Synlett, (16), 2498-2502. https://doi.org/10.1055/s-0030-1258547