title: Synthesis of Diarylheptanoid Scaffolds Inspired by Calyxins I and J.
abstract: γ,δ-Unsaturated alcohols are prepared efficiently in two steps from o-hydroxycinnamaldehyde. The TMSOTf-mediated reaction of the γ,δ-unsaturated alcohols with aldehydes creates two oxygen heterocycles and three new stereocenters in a single pot. The approach is versatile, and by varying the boronic acid, Grignard reagent, and aldehyde, different substituents may be introduced, while use of a chiral base in the conjugate addition gives enantioenriched products.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Ackrill
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
authors.forename: Hazel A
authors.initials: HA
authors.lastname: Sparkes
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, U.K.
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry; D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D002934:Cinnamates; D036381:Diarylheptanoids; C410688:calyxin I; C545382:calyxin J; C117045:p-hydroxycinnamaldehyde