title: Efficient and selective synthesis of siphonarienolone and related reduced polypropionates via Zr-catalyzed asymmetric carboalumination.
abstract: [reaction: see text] Siphonarienolone (1) has been synthesized from siphonarienal (3) in 66% over four steps. Synthesis of 3, in turn, has been achieved in two steps (85% combined yield) from 4, prepared from 3-buten-1-ol in seven steps (23% combined yield). Also, a two-step conversion of 3 into siphonarienone (2) is reported.
authors.affiliation: Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
authors.forename: Marina
authors.initials: M
authors.lastname: Magnin-Lachaux
authors.forename: Ze
authors.initials: Z
authors.lastname: Tan
authors.forename: Bo
authors.initials: B
authors.lastname: Liang
authors.forename: Ei-Ichi
authors.initials: E
authors.lastname: Negishi
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis*; D000535:Aluminum / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis*; D011422:Propionates / Q000737:chemistry*; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
chemical_list: D000473:Alkanes; D007659:Ketones; D011422:Propionates; C470331:siphonarienolone; D002244:Carbon; D015040:Zirconium; D000535:Aluminum