title: Asymmetric total synthesis of bacillariolide III, a marine oxylipin.
abstract: [reaction: see text] The asymmetric total synthesis of bacillariolide III has been achieved via 15 linear steps in 14.6% overall yield. The key feature of this synthetic route involves the highly stereoselective construction of the vinyl-substituted bicyclic lactone by an intramolecular Pd(0)-catalyzed allylic alkylation and its facile conversion to the hydroxy bicyclic lactone skeleton of bacillariolide III, induced by stereoselective vinylcerium addition to the aldehyde. In addition, the (Z)-pentenoic acid was efficiently introduced by the internal hydroxy group tethered ring-closing metathesis (RCM).
authors.affiliation: College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
authors.forename: Seung-Yong
authors.initials: SY
authors.lastname: Seo
authors.forename: Jae-Kyung
authors.initials: JK
authors.lastname: Jung
authors.forename: Seung-Mann
authors.initials: SM
authors.lastname: Paek
authors.forename: Yong-Sil
authors.initials: YS
authors.lastname: Lee
authors.forename: Seok-Ho
authors.initials: SH
authors.lastname: Kim
authors.forename: Kwang-Ok
authors.initials: KO
authors.lastname: Lee
authors.forename: Young-Ger
authors.initials: YG
authors.lastname: Suh
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D017377:Diatoms / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007783:Lactones; C485138:bacillariolide III