Studies toward the synthesis of pinnatoxins: the B,C,D-dispiroketal fragment.
A stereoselective synthesis of the tricyclic B,C,D-dispiroketal fragment of pinnatoxins is described. Both products of an efficient enzymatic resolution reaction are used to set the stereochemistry of C12 and C23, which have opposite configuration. The configuration of the ketal centers is established upon an optimized thermodynamically controlled spiroketalization.
Lu
Chong-Dao
CD
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
Zakarian
Armen
A
D000470:Alkaloids; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
D000470:Alkaloids; D013141:Spiro Compounds; C519414:pinnatoxin B