title: Total Synthesis and Determination of the Absolute Configuration of Naturally Occurring Mangromicin A, with Potent Antitrypanosomal Activity.
abstract: An enantioselective total synthesis of (+)-mangromicin A has been accomplished. The tetrahydrofuran ring of mangromicin A, possessing a tetrasubstituted carbon center, was constructed by Mukaiyama-type vinylogous alkylation via a cyclic oxocarbenium intermediate derived from a γ-hydroxy ketone with ideal stereoselectivity, and the 4-hydroxydihydropyrone scaffold was generated via Dieckmann cyclization at a late stage of the total synthesis. The reliable asymmetric synthesis of (+)-mangromicin A has revealed the absolute configuration of naturally occurring mangromicin A.
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Takada
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yamada
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Tomoyasu
authors.initials: T
authors.lastname: Hirose
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Takuma
authors.initials: T
authors.lastname: Ishihara
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Takuji
authors.initials: T
authors.lastname: Nakashima
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Yo Ko
authors.initials: YK
authors.lastname: Takahashi
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Satoshi
authors.initials: S
authors.lastname: O Mura
authors.affiliation: Graduate School of Infection Control Sciences and Kitasato Institute for Life Sciences, Kitasato University , 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Toshiaki
authors.identifier: 0000-0003-3452-6070
authors.initials: T
authors.lastname: Sunazuka
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002384:Catalysis; D003500:Cyclization; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011753:Pyrones / Q000737:chemistry; D013237:Stereoisomerism; D014344:Trypanocidal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D014346:Trypanosoma brucei brucei / Q000187:drug effects
chemical_list: D000447:Aldehydes; D000900:Anti-Bacterial Agents; D018942:Macrolides; D011753:Pyrones; D014344:Trypanocidal Agents; C000588478:mangromicin A