title: Tandem intramolecular Michael-aldol reaction as a tool for the construction of the C-ring of hexacyclinic acid.
abstract: [reaction: see text] The tandem intramolecular Michael-aldol reaction was studied as a tool for the construction of the C-ring of hexacyclinic acid. By changing the reaction conditions it was possible to selectively obtain either the kinetic or the thermodynamic product. Retro-aldol reaction and subsequent epimerization provides four individual cyclopentane derivatives that can be incorporated as building blocks in natural product syntheses.
authors.affiliation: Institute of Organic Chemistry, University of Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
authors.forename: Andriy
authors.initials: A
authors.lastname: Stelmakh
authors.forename: Timo
authors.initials: T
authors.lastname: Stellfeld
authors.forename: Markus
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry
chemical_list: D006576:Heterocyclic Compounds, 4 or More Rings; D018942:Macrolides; C502347:hexacyclinic acid