title: Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A.
abstract: A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presence of 10 mol% trimethylsilyltriflate under mild conditions. The salient features of this methodology are high yields, excellent selectivity, low catalyst loading and faster reaction times. This method has been successfully applied to the total synthesis of pyranopyran, tetraketide and polyrhacitide A.
authors.affiliation: Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
authors.forename: B V
authors.initials: BV
authors.lastname: Subba Reddy
authors.affiliation: Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
authors.forename: Dhanraj O
authors.initials: DO
authors.lastname: Biradar
authors.affiliation: Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
authors.forename: Y
authors.initials: Y
authors.lastname: Vikram Reddy
authors.affiliation: Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in.
authors.forename: J S
authors.initials: JS
authors.lastname: Yadav
authors.affiliation: Centre for Nuclear Magnetic Resonance, Hyderabad -500 007, India.
authors.forename: Kiran Kumar
authors.initials: KK
authors.lastname: Singarapu
authors.affiliation: Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad -500 007, India.
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003512:Cyclohexanones; D004187:Disaccharides; D007783:Lactones; D011714:Pyrans; D014297:Trimethylsilyl Compounds; C529416:polyrhacitide A; C413265:tetraketide