title: A concise and unified strategy for synthesis of the C1-C18 macrolactone fragments of FD-891, FD-892 and their analogues: formal total synthesis of FD-891.
abstract: A concise and unified strategy for the synthesis of C1-C18 macrolactone fragments of FD-891 and FD-892 as well as their analogues is reported. The strategy includes a stereoselective vinylogous Mukaiyama aldol reaction (VMAR) using chiral silyl ketene N,O-acetal to construct C6-C7 stereocenters, an E-selective ring closing metathesis to construct a C12-C13 olefin, and stereodivergent construction of a C8-C9 epoxide.
authors.affiliation: Graduate School of Pharmaceutical Sciences and ‡Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University , 6-3 Aza-Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Naoki
authors.initials: N
authors.lastname: Kanoh
authors.forename: Ayano
authors.initials: A
authors.lastname: Kawamata
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Itagaki
authors.forename: Yuta
authors.initials: Y
authors.lastname: Miyazaki
authors.forename: Kenzo
authors.initials: K
authors.lastname: Yahata
authors.forename: Eunsang
authors.initials: E
authors.lastname: Kwon
authors.forename: Yoshiharu
authors.initials: Y
authors.lastname: Iwabuchi
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007783:Lactones; D018942:Macrolides; C091118:FD 891; C091119:FD 892; C116609:3-hydroxybutanal