benzofurans and 3-hydroxybutanal

A highly enantioselective Michael-aldol tandem reaction with respect to prochiral 2-substituted benzofuran-3-ones and enones by a facile primary amine catalyst was investigated. The approach provides rapid access to the desired pharmaceutically active griseofulvin analogues.

Topics: Aldehydes; Amines; Benzofurans; Catalysis; Griseofulvin; Molecular Structure; Spiro Compounds; Stereoisomerism

Topics: Alcohols; Aldehydes; Benzofurans; Catalysis; Crystallography, X-Ray; Molecular Conformation; Oxygen; Stereoisomerism

The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.

Topics: Aldehydes; Benzofurans; Bignoniaceae; Catalysis; Crystallography, X-Ray; Furans; Heterocyclic Compounds, 2-Ring; Heterocyclic Compounds, 4 or More Rings; Molecular Structure; Stereoisomerism

Topics: Aldehydes; Antineoplastic Agents; Benzofurans; Biological Products; Crystallography, X-Ray; Cyclization; Hydrogen-Ion Concentration; Lactic Acid; Molecular Conformation; Paecilomyces; Spiro Compounds; Tubulin Modulators