Access to both anomers of pectenotoxin spiroketals by kinetic spiroketalization.
[structure: see text] A concise synthesis of both AB ring spiroisomers of the pectenotoxins is described. The nonanomeric AB spiroketal ring system of the pectenotoxins-1, -2, -3, and -6 is formed under very mild, kinetic spiroketalization conditions, along with the anomeric isomer. Only catalytic asymmetric transformations were used as the source of chirality in the synthesis route.
Laboratory of Organic Chemistry, Helsinki University of Technology, P.O.B. 6100, FI-02015 HUT, Finland. petri.pihko@hut.fi
Petri M
PM
Pihko
Jatta E
JE
Aho
D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
D008387:Marine Toxins; D011714:Pyrans