title: Total syntheses of Prelactone V and Prelactone B.
abstract: The total syntheses of natural products Prelactone-V and Prelactone-B have been accomplished by a novel Chiron approach starting from d-glucose. The synthesis involves isopropylidene acetal formation of d-glucose using Poly(4-vinylpyridine) supported iodine as a catalyst, Tebbe olefination, Grignard reaction, Wittig olefination, selective mono deprotection of acetal using PMA/SiO2, hydrogenation and anti-1,3-diol formation are as key steps.
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India; Dept. of Pharmaceutical Chemistry, School of Pharmacy and Health Sciences, International Medical University, Kuala Lumpur, 57000, Malaysia. Electronic address: srgoud2@gmail.com.
authors.forename: S
authors.initials: S
authors.lastname: Raghavendra
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India; Department of Chemistry, Christ University, Hosur Road, Bangalore, 560029, India.
authors.forename: Krishnaji
authors.initials: K
authors.lastname: Tadiparthi
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, 500007, India.
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
mesh_terms: D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D007783:Lactones; C523059:prelactone B; C000617152:prelactone V
keywords: Grignard reaction and Tebbe reaction; Lactonisation; P(4-VPI)(+)I(3)(−); PMA/SiO(2); Wittig olefination; d-glucose