title: cis-decalins from quinic acid: toward a synthesis of branimycin.
abstract: [reaction: see text] Starting from (-)-quinic acid an efficient synthesis of highly functionalized cis-alpha,beta-unsaturated ketone 3, an advanced precursor of branimycin, has been accomplished via two key step reactions: a ring closing metathesis reaction to prepare the cis-decalin system, and a highly stereoselective epoxidation reaction.
authors.affiliation: Institut für Organische Chemie, Währingerstrasse 38, A-1090 Wien, Austria.
authors.forename: Stefan
authors.initials: S
authors.lastname: Marchart
authors.forename: Johann
authors.initials: J
authors.lastname: Mulzer
authors.forename: Valentin S
authors.initials: VS
authors.lastname: Enev
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D011801:Quinic Acid / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D007659:Ketones; D018942:Macrolides; D009281:Naphthalenes; C516575:branimycin; D011801:Quinic Acid; C007229:decalin