Practical total synthesis of fuligocandins A and B

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

Research output: Contribution to journalArticlepeer-review

10 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
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Practical total synthesis of fuligocandins A and B'. Together they form a unique fingerprint.

Cite this