title: Concise synthesis of stagonolide-F by ring closing metathesis approach and its biological evaluation.
abstract: The first total synthesis of 9-membered macrolide, stagonolide-F (3), starting from commercially available 1,5-pentane diol is reported. A combination of Jacobsen's hydrolytic kinetic resolution (HKR) and Sharpless epoxidation is used for the creation of two stereogenic centers, while ring-closing metathesis (RCM) strategy was used for the construction of the lactone ring. The molecule synthesized exhibited potent antifungal, antibacterial and cytotoxic activities against all the tested strains.
authors.affiliation: Organic Chemistry Division-II, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500 607, Andhra Pradesh, India. aruniict@gmail.com
authors.forename: Arun Kumar
authors.initials: AK
authors.lastname: Perepogu
authors.forename: D
authors.initials: D
authors.lastname: Raman
authors.forename: U S N
authors.initials: US
authors.lastname: Murty
authors.forename: Vaidya Jayathirtha
authors.initials: VJ
authors.lastname: Rao
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D003500:Cyclization; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism
chemical_list: C540870:5-hydroxy-9-methyl-6-nonen-9-olide; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006573:Heterocyclic Compounds, 1-Ring; D007783:Lactones; D018942:Macrolides; C527511:stagonolide