title: A protecting-group-free synthesis of Hagen's gland lactones.
abstract: A practical protecting group free synthesis of Hagen's gland lactones 1 and 2 is accomplished in four steps and 25.6 and 37.4% overall yields, respectively. The strategy relies on a one-pot conversion of D-glucono-δ-lactone to β-hydroxy-γ-vinyl-γ-lactone, cross-metathesis, and iodocyclization-deiodinization as key steps.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, Maharashtra, India. rfernand@chem.iitb.ac.in
authors.forename: Rodney A
authors.initials: RA
authors.lastname: Fernandes
authors.forename: Pullaiah
authors.initials: P
authors.lastname: Kattanguru
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D007783:Lactones