Synthesis of the non-classical acetogenin mucocin: a modular approach based on olefinic coupling reactions.
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.
Zhu
Lei
L
Department of Chemistry, Hunter College, 695 Park Avenue, New York, NY 10021, USA.
Mootoo
David R
DR
D000475:Alkenes / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D007783:Lactones; D011714:Pyrans; C413144:mucocin