title: A concise, stereocontrolled total synthesis of rippertenol.
abstract: The first total synthesis of the unique terpene rippertenol, a molecule with dense stereochemical complexity arrayed on a compact framework largely devoid of functional groups, is described. Key elements include orchestrated and unique applications of aldol condensations, Diels-Alder chemistry, and a ring expansion to advance a chiral starting material containing a single chiral center into the final target in a concise and diastereocontrolled manner.
authors.affiliation: Department of Chemistry, Columbia University, Havemeyer Hall, 3000 Broadway, New York, New York 10027, USA. sas2197@columbia.edu
authors.forename: Scott A
authors.initials: SA
authors.lastname: Snyder
authors.forename: Daniel A
authors.initials: DA
authors.lastname: Wespe
authors.forename: J Marian
authors.initials: JM
authors.lastname: von Hof
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D004224:Diterpenes; D007659:Ketones; D013729:Terpenes