Total synthesis and conformational analysis of the antifungal agent (-)-PF1163B.
[reaction: see text]. (-)-PF1163B, a new macrocyclic antifungal antibiotic isolated from Streptomyces sp., has been prepared in eight steps from (S)-citronellene. The key step is a ring-closing metathesis reaction of an ester and amide derivative obtained from a substituted N-methyl-l-tyrosine.
Bouazza
Fodil
F
UMR 6514, University of Poitiers and CNRS, 40 avenue du recteur Pineau, 86022 Poitiers, France.
Renoux
Brigitte
B
Bachmann
Christian
C
Gesson
Jean-Pierre
JP
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D047028:Macrocyclic Compounds; D009682:Magnetic Resonance Spectroscopy; D008781:Methyltyrosines / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D006573:Heterocyclic Compounds, 1-Ring; D047028:Macrocyclic Compounds; D008781:Methyltyrosines; D039821:Monoterpenes; C405058:PF 1163B