title: Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions.
abstract: A three component modular synthesis of the potent antitumor agent mucocin, based on olefinic coupling reactions, is described. A cross-metathesis on tetrahydropyran and tetrahydrofuran alkene components was used to assemble a stereochemically complex, non-adjacently-linked bicyclic ether. The latter was elaborated to a sulfone and partnered with a butenolide aldehyde component in a Julia-Kocienski olefination to provide the mucocin framework, which was converted to the natural product after hydrogenation and alcohol deprotection.
authors: Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10021, USA.
authors: Lei
authors: L
authors: Zhu
authors: David R
authors: DR
authors: Mootoo
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D007783:Lactones; D011714:Pyrans; C413144:mucocin