An approach to the imine ring system of pinnatoxins.
[reaction: see text] A concise stereoselective approach to the spirobicyclic imine fragment of pinnatoxins and pteriatoxins is described. The approach relies on a tandem reaction sequence involving consecutive sigmatropic rearrangements to build the quaternary chiral center at the core of the spirobicyclic ring system.
Pelc
Matthew J
MJ
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
Zakarian
Armen
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D007097:Imines; D013141:Spiro Compounds; C447983:pinnatoxin A