title: Enantioselective syntheses of tremulenediol A and tremulenolide A.
abstract: [reaction: see text] An enantioselective entry to the skeleton of the tremulane sesquiterpenes is described. The approach features a series of efficient transition metal-catalyzed reactions commencing with an enantioselective rhodium(II)-catalyzed intramolecular cyclopropanation followed by a regioselective allylic alkylation and a diastereoselective rhodium(I)-catalyzed [5 + 2] cycloaddition. This strategy was applied to the first enantioselective syntheses of tremulenediol A and tremulenolide A.
authors.affiliation: Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA.
authors.forename: Brandon L
authors.initials: BL
authors.lastname: Ashfeld
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Martin
mesh_terms: D000478:Alkylation; D002244:Carbon / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D008314:Malonates; D009930:Organic Chemicals; D012717:Sesquiterpenes; C512231:tremulenediol A; C512232:tremulenolide A; D002244:Carbon; C030290:malonic acid