title: Total synthesis of (-)-exiguolide.
abstract: The first total synthesis of the naturally occurring enantiomer of exiguolide ((-)-1) has been completed. This very convergent synthesis features the following as main steps: (i) a Trost's ruthenium-catalyzed ene-yne cross-coupling reaction (this complex transformation allows the challenging control of the C5-C28 double bond geometry along with the stereoselective construction of the tetrahydropyran ring A) and (ii) a very efficient one-pot, two-step stereoselective conjugated allylic alcohol substitution that allowed the control of the C15 stereogenic center.
authors.affiliation: Centre de Recherche CNRS de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Cyril
authors.initials: C
authors.lastname: Cook
authors.forename: Xavier
authors.initials: X
authors.lastname: Guinchard
authors.forename: Frédéric
authors.initials: F
authors.lastname: Liron
authors.forename: Emmanuel
authors.initials: E
authors.lastname: Roulland
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D018942:Macrolides; D009942:Organometallic Compounds; C527475:exiguolide; D012428:Ruthenium