title: Stereoselective construction of all-anti polypropionate modules: synthesis of the C5-C10 fragment of streptovaricin U.
abstract: A concise nonaldol approach for the stereoselective construction of all-anti polypropionate fragments was developed. The iterative epoxide-based methodology consists of the syn-selective epoxidation of cis homoallylic alcohols with use of the VO(acac)(2)-catalyzed conditions followed by epoxide cleavage with a propynyl aluminum reagent as key steps. The methodology was applied to the synthesis of the all-anti C6-C10 fragment of streptovaricin U.
authors.affiliation: Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, P.O. Box 23346, San Juan, Puerto Rico.
authors.forename: Wildeliz
authors.initials: W
authors.lastname: Torres
authors.forename: Raúl R
authors.initials: RR
authors.lastname: Rodríguez
authors.forename: José A
authors.initials: JA
authors.lastname: Prieto
mesh_terms: D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D018942:Macrolides; D011422:Propionates; C525797:streptovaricin U