title: A novel Prins cascade process for the stereoselective synthesis of oxa-bicycles.
abstract: E- and Z-9-Methyldeca-3,8-dien-1-ols undergo smooth cyclization with aldehydes in the presence of 20 mol% AgSbF6 under extremely mild conditions to generate the corresponding oxa-bicycles in good yields with excellent selectivity. In fact, E-olefin affords the trans-product exclusively, whereas the Z-olefin gives the cis-product predominantly. In the case of E- or Z-8-methylnona-3,8-dien-1-ol, the product is formed via the termination of Prins cyclization with an allylic C-H bond through olefin migration. The termination of Prins cyclization with tethered olefin is an unprecedented reaction, which provides a useful motif of various natural products.
authors.affiliation: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. basireddy@iict.res.in.
authors.forename: B V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: A
authors.initials: A
authors.lastname: Venkateswarlu
authors.forename: B
authors.initials: B
authors.lastname: Sridevi
authors.forename: Kanakaraju
authors.initials: K
authors.lastname: Marumudi
authors.forename: A C
authors.initials: AC
authors.lastname: Kunwar
authors.forename: G
authors.initials: G
authors.lastname: Gayatri
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds