Synthesis of the azaspiracid-1 trioxadispiroketal.
The de novo analysis, design, and synthesis of the azaspiracid-1 trioxadispiroketal system is described. A revised structural model was developed on the basis of an independent analysis of the NMR spectral data of the natural product that fit all of the data and the thermodynamically favored spiroketal paradigm. This model was then tested via synthesis using a novel trioxadispiroketalization process and supported by spectroscopic correlation.
Geisler
Lisa K
LK
Department of Chemistry, Institute of Technology, University of Minnesota, 207 Pleasant Street S.E., Minneapolis, Minnesota 55113, USA.
Nguyen
Son
S
Forsyth
Craig J
CJ
D005663:Furans / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000138:chemical synthesis*; D008958:Models, Molecular; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D005663:Furans; D008387:Marine Toxins; D013141:Spiro Compounds; C406592:azaspiracid; D000095702:Polyether Toxins; C507607:trioxadispiroketal