title: Total Synthesis of (+)-Goniodenin.
abstract: Goniodenin is a lipophilic polyketide originating from plant sources and which possesses a potent cytotoxic activity against cancer cell lines. The first total synthesis of (+)-goniodenin has been achieved in 23 steps from (R)-glycidol. The synthetic sequence featured a cross metathesis for the formation of the C8-C9bond and installation of the terminal γ-butenolactone ring unit by the alkylation of α-phenylthio-γ-butyrolactone with the corresponding C3-O-triflate. The stereogenic center at C18carbon was created by Hiyama-Fujita reduction of the corresponding ketone with high diastereoselectivity.
authors.affiliation: Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Ueda
authors.affiliation: Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Ai
authors.initials: A
authors.lastname: Suzuki
authors.affiliation: Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Mai
authors.initials: M
authors.lastname: Sasaki
authors.affiliation: Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Naoyuki
authors.initials: N
authors.lastname: Hoshiya
authors.affiliation: Kyoto Pharmaceutical University , Shichonocho 1, Misasagi, Yamashina, Kyoto, 607-8412, Japan.
authors.forename: Jun'ichi
authors.identifier: 0000-0002-7012-3482
authors.initials: J
authors.lastname: Uenishi
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry; D054378:Acetogenins / Q000138:chemical synthesis*; D000478:Alkylation; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D003500:Cyclization; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066244:Proton Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
chemical_list: D054378:Acetogenins; D061065:Polyketides; C000627194:goniodenin; D015107:4-Butyrolactone