Total synthesis of the proposed structure for spirofungin B: a reassignment of the stereochemistry.
[structure: see text] The total synthesis of the proposed structure for spirofungin B (2) is described. The data for the synthetic material did not compare with that for the natural product leading to the conclusion that the structure 2 assigned for spirofungin B is incorrect. Analysis of the NMR data reported for spirofungins A and B as well as related spiroketals allowed for the reassignment of the stereochemistry of spirofungin B to be that corresponding to 15-epi-spirofungin A (27).
Zanatta
Shannon D
SD
School of Chemistry, The University of Melbourne, Victoria 3010, Australia.
White
Jonathan M
JM
Rizzacasa
Mark A
MA
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000935:Antifungal Agents; D011714:Pyrans; D013141:Spiro Compounds; C114877:spirofungin A; C493365:spirofungin B