title: The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues.
abstract: The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactonization reaction and CBS reduction as the key steps. In this article, we have observed the most suitable protecting groups with respect to selectivity during the protecting group directed intermolecular asymmetric Nozaki-Hiyama-Kishi reaction. The zeaenol, 7-epi-zeaenol and its derivatives were analyzed for their biological activity and screened in four cancer cell lines.
authors.affiliation: Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. mohapatra@iict.res.in.
authors.forename: Debendra K
authors.initials: DK
authors.lastname: Mohapatra
authors.forename: D Sai
authors.initials: DS
authors.lastname: Reddy
authors.forename: N Arjunreddy
authors.initials: NA
authors.lastname: Mallampudi
authors.forename: Janardhan
authors.initials: J
authors.lastname: Gaddam
authors.forename: Sowjanya
authors.initials: S
authors.lastname: Polepalli
authors.forename: Nishant
authors.initials: N
authors.lastname: Jain
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001203:Ascomycota / Q000737:chemistry; D045744:Cell Line, Tumor; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D013237:Stereoisomerism; D015025:Zearalenone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000008:administration & dosage; D007783:Lactones; D012118:Resorcinols
chemical_list: D000970:Antineoplastic Agents; D015025:Zearalenone; C505734:7-oxozeanol; D007783:Lactones; D012118:Resorcinols