title: Complete Stereochemical Assignment of Campechic Acids A and B.
abstract: Campechic acids A and B are anti-invasive polyketide antibiotics isolated from Streptomyces sp. CHI93 strain. Herein we describe stereoselective synthesis of the C-16-C-30 fragment of campechic acids A and B via a biosynthesis-inspired epoxide-opening cascade and its NMR spectroscopic comparison with the authentic degradation product, resulting in configurational assignment of the C-21, C-24, C-25, and C-28 stereogenic centers and reassignment of the C-18 stereogenic center.
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan.
authors.forename: Ruri
authors.initials: R
authors.lastname: Isaka
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University , 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
authors.forename: Linkai
authors.initials: L
authors.lastname: Yu
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
authors.affiliation: Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University , 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Igarashi
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai, Miyagi 980-8577, Japan.
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D001688:Biological Products; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D061065:Polyketides / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D001688:Biological Products; D004852:Epoxy Compounds; D061065:Polyketides; C000589784:campechic acid A; C000589785:campechic acid B