title: Synthesis of Strained 1,3-Diene Macrocycles via Copper-Mediated Castro-Stephens Coupling/Alkyne Reduction Tandem Reactions.
abstract: A copper-mediated macrocyclization involving the reaction of a vinyl iodide and a terminal alkyne followed by an in situ reduction of the enyne intermediate is reported. The reaction generates a conjugated Z-double bond within a strained medium-size lactone, lactam, or ether macrocycle. A variety of macrocyclic compounds bearing different ring sizes and functionalities were synthesized. A complementary stepwise procedure was also developed for less strained ring systems.
authors.affiliation: †Department of Chemistry, Department of Medicinal Chemistry, and the Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.affiliation: ‡Department of Medicinal Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045, United States.
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Schneider
authors.affiliation: †Department of Chemistry, Department of Medicinal Chemistry, and the Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, United States.
authors.forename: Gunda I
authors.initials: GI
authors.lastname: Georg
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D047028:Macrocyclic Compounds; D003300:Copper