title: Total synthesis of the leucosceptroid family of natural products.
abstract: A highly efficient strategy enabled the asymmetric total synthesis of 15 antifeedant leucosceptroid natural products. The advanced tricyclic core, available in gram quantity, served as the pivotal intermediate for the preparation of norleucosceptroids B, C, F, and G and leucosceptroids A, B, G, I, J, L, and M. Additionally, the bioinspired oxidative transformation of leucosceptroid A to leucosceptroids C, K, O, and P using singlet oxygen supports the hypothesis that leucosceptroids A and B are most likely the biogenetic precursors of all other members of this natural product family.
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Cedric L
authors.initials: CL
authors.lastname: Hugelshofer
authors.affiliation: Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstrasse 5-13, 81377 Munich, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Magauer
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D054830:Sesterterpenes / Q000138:chemical synthesis*
chemical_list: D001688:Biological Products; D054830:Sesterterpenes; D010100:Oxygen