title: Asymmetric synthesis of (+)-geranyllinaloisocyanide: assignment of absolute stereochemistry.
abstract: The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (-)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.
authors.affiliation: Faculty of Science, Kochi University, Akebono-cho, Kochi, Japan. ichikawa@kochi-u.ac.jp
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Ichikawa
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Matsuda
authors.forename: Ken
authors.initials: K
authors.lastname: Okumura
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Nakamura
authors.forename: Toshiya
authors.initials: T
authors.lastname: Masuda
authors.forename: Hiyoshizo
authors.initials: H
authors.lastname: Kotsuki
authors.forename: Keiji
authors.initials: K
authors.lastname: Nakano
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D004952:Esters; D006254:Hawaii; D019344:Lactic Acid / Q000031:analogs & derivatives* / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D004952:Esters; D009570:Nitriles; C559226:geranyllinaloisocyanide; D019344:Lactic Acid