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.
Pihko
Petri M
PM
Laboratory of Organic Chemistry, Helsinki University of Technology, P.O.B. 6100, FI-02015 HUT, Finland. petri.pihko@hut.fi
Aho
Jatta E
JE
D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
D008387:Marine Toxins; D011714:Pyrans