title: Synthetic studies of an 18-membered antitumor macrolide, tedanolide. 5. Stereoselective synthesis of the C13-C23 part via condensation of two fragments, C13-C17 and C18-C21, by taking advantage of the 3,4-dimethoxybenzyl protecting group.
abstract: An efficient and stereoselective synthesis of the C13-C23 part (8) was achieved starting from methyl (R)- and (S)-3-hydroxy-2-methylpropionates (9) via coupling of the C13-C17 aldehyde (6), prepared by Evans asymmetric aldol reaction, with the C18-C21 iodoalkene (5b) by taking advantage of the 3,4-dimethoxybenzyl protecting group.
authors.affiliation: Department of Chemistry, Okayama University of Science, Japan.
authors.forename: B Z
authors.initials: BZ
authors.lastname: Zheng
authors.forename: H
authors.initials: H
authors.lastname: Maeda
authors.forename: M
authors.initials: M
authors.lastname: Mori
authors.forename: S
authors.initials: S
authors.lastname: Kusaka
authors.forename: O
authors.initials: O
authors.lastname: Yonemitsu
authors.forename: T
authors.initials: T
authors.lastname: Matsushima
authors.forename: N
authors.initials: N
authors.lastname: Nakajima
authors.forename: J
authors.initials: J
authors.lastname: Uenishi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D007783:Lactones / Q000138:chemical synthesis / Q000494:pharmacology; D018942:Macrolides; D010084:Oxidation-Reduction; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D007783:Lactones; D018942:Macrolides; C119775:tedanolide