Filipin III: Configuration Assignment and Confirmation by Synthetic Correlation
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (13) , 4219-4231
- https://doi.org/10.1021/jo960218x
Abstract
The stereochemical configuration of filipin III (1) was determined using the (13)C acetonide analysis. The relative configurations for the nine stereogenic centers in the top half of filipin were initially identified using just three acetonide derivatives (2, 3, and 4) arising from a two-step protection sequence. The structure was confirmed by synthesis and direct correlation of degradation products 8 (C26-C28) and 10 (C1-C16). Filipin tetraacetonide 2 and triacetonide 4 each contain an anti acetonide in a highly unusual chair conformation. Molecular modeling successfully reproduced the preference for a chair conformation over the normally more stable twist-boat conformation.Keywords
This publication has 26 references indexed in Scilit:
- How do the polyene macrolide antibiotics affect the cellular membrane properties?Published by Elsevier ,2003
- Fluorescence study of the macrolide pentaene antibiotic filipin in aqueous solution and in a model system of membranesEuropean Journal of Biochemistry, 1992
- Rearrangement of N-(alkylamino)azoles in acid media: a new entry to C-amino-N-substituted azolesThe Journal of Organic Chemistry, 1992
- High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoidsJournal of the American Chemical Society, 1991
- Synthesis of (2R,3S)‐1,2,3‐Butanetriol Derivatives From (R)‐2,3‐O‐Isopropylideneglyceraldehyde and of the (2S,3R)‐Enantiomers From D‐Glucose. Application to the Synthesis of Enantiomerically Pure MuscarineEuropean Journal of Organic Chemistry, 1987
- Reaction of some azolopyrido[2,3-d]pyrimidines with active methylene compoundsThe Journal of Organic Chemistry, 1983
- Detection of microdomains in biomembranes An appraisal of recent developments in freeze-fracture cytochemistryBiochimica et Biophysica Acta (BBA) - Reviews on Biomembranes, 1983
- Carbon-13 chemical shifts: sensitive detectors in structure determination. Part 2. Carbon-13 nuclear magnetic resonance chemical shifts and the twist conformations of 1,3-dioxanes. Geminal substitution at the 4-position: a guaranty for the chair form?The Journal of Organic Chemistry, 1982
- Polyene antibiotics. IV. Structure of chaininJournal of the American Chemical Society, 1972
- Filipin, an Antifungal Antibiotic: Isolation and PropertiesJournal of the American Chemical Society, 1955