title: A domino-based approach toward stereodefined heavily functionalized cyclohexanes: synthesis of iridal's core structure.
abstract: A stereoselective synthesis of heavily functionalized six-membered ring subunits, which possess functionality at sites appropriate for further elaboration, is described. The cyclopentanone moiety of hydrindenediol is required to achieve total facial selectivity during the pre-domino installation of the second quaternary center, while oxidative cleavage is responsible for the ring-expanding rearrangement. A microwave-assisted version of the key domino transformation and a test of concept approach toward the iridal core structure are also presented.
authors.affiliation: Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, Gif-sur-Yvette, France.
authors.forename: Andrei
authors.initials: A
authors.lastname: Corbu
authors.forename: Guillaume
authors.initials: G
authors.lastname: Gauron
authors.forename: Juan M
authors.initials: JM
authors.lastname: Castro
authors.forename: Mohamed
authors.initials: M
authors.lastname: Dakir
authors.forename: Siméon
authors.initials: S
authors.lastname: Arseniyadis
mesh_terms: D003510:Cyclohexanes / Q000138:chemical synthesis / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D003510:Cyclohexanes; D014315:Triterpenes; C473636:iridal; D010100:Oxygen