title: Synthesis of the Bioherbicidal Fungus Metabolite Macrocidin A.
abstract: The second total synthesis of macrocidin A afforded the bioherbicidal fungal metabolite in 16 steps starting from doubly protected l-tyrosine. The 3-octanoyl side chain with the α-methyl group and an ω-bromo epoxide already in place was attached to the tetramic acid via a Yoshii-Yoda acylation, and the macrocycle was eventually closed in 55% yield by a Williamson etherification between the phenolate and the epoxy bromide.
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth , Universitätsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Robert G
authors.initials: RG
authors.lastname: Haase
authors.affiliation: Organic Chemistry Laboratory, University of Bayreuth , Universitätsstrasse 30, 95440 Bayreuth, Germany.
authors.forename: Rainer
authors.identifier: 0000-0002-8413-4342
authors.initials: R
authors.lastname: Schobert
mesh_terms: D001203:Ascomycota / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism; D000097566:Cyclophanes
chemical_list: D011760:Pyrrolidinones; C482758:macrocidin A; D000097566:Cyclophanes