title: Synthesis and structural reassignment of (+)-epicalyxin F.
abstract: We have established the structure of (+)-epicalyxin F through chemical synthesis. An acid-promoted rearrangement of synthetic benzopyran 6 led to the identification of the natural product as (3S,5S,7R)-epicalyxin F (22). Comparison with NMR spectra and optical rotation of the natural product confirms our assignment, and the reassigned structure is compatible with the proposed biosynthetic pathway.
authors.affiliation: Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
authors.forename: Xia
authors.initials: X
authors.lastname: Tian
authors.forename: Scott D
authors.initials: SD
authors.lastname: Rychnovsky
mesh_terms: D036381:Diarylheptanoids / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D036381:Diarylheptanoids; C410689:epicalyxin F