title: Studies toward the synthesis of pinnatoxins: the B,C,D-dispiroketal fragment.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
authors.forename: Chong-Dao
authors.initials: CD
authors.lastname: Lu
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D000470:Alkaloids; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D000470:Alkaloids; D013141:Spiro Compounds; C519414:pinnatoxin B