title: A minimalist NMR approach for the structural revision of mucoxin.
abstract: In an attempt to revise the structural assignment of mucoxin, and faced with 64 diastereomeric possibilities, we resorted to the synthesis of truncated structures that contained the core stereochemical sites. Twelve stereochemical analogues were synthesized, their (1)H and (13)C NMR spectra were analyzed and four recurring stereochemical trends were distilled from the data. Applying the observed trends to the diastereomeric population pared the possible choices for the correct structure of mucoxin from 64 to 4. Synthesis of these analogues led to the identification of the correct structure of mucoxin.
authors.affiliation: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors.forename: Jun
authors.initials: J
authors.lastname: Yan
authors.forename: Atefeh
authors.initials: A
authors.lastname: Garzan
authors.forename: Radha S
authors.initials: RS
authors.lastname: Narayan
authors.forename: Chrysoula
authors.initials: C
authors.lastname: Vasileiou
authors.forename: Babak
authors.initials: B
authors.lastname: Borhan
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005663:Furans; C515333:mucoxin