title: Total synthesis of marinomycin A based on a direct dimerization strategy.
abstract: The asymmetric total synthesis of (+)-marinomycin A, a 44-membered macrodiolide antitumor agent and antibiotic isolated from a marine actinomycete, Marinispora strain CNQ-140, is reported. The key features of the synthesis include the highly convergent stereocontrolled construction of the monomeric hydroxy salicylate starting from asymmetric epoxidation of the σ-symmetrical dialkenyl carbinol, and an unprecedented direct dimerization through NaHMDS-promoted double transesterification.
authors: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521 (Japan).
authors: Tatsuya
authors: T
authors: Nishimaru
authors: Masashi
authors: M
authors: Kondo
authors: Kimito
authors: K
authors: Takeshita
authors: Keisuke
authors: K
authors: Takahashi
authors: Jun
authors: J
authors: Ishihara
authors: Susumi
authors: S
authors: Hatakeyama
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D019281:Dimerization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000900:Anti-Bacterial Agents; D001688:Biological Products; D018942:Macrolides; C509125:marinomycin A
keywords: antibiotics; antitumor agents; macrodiolides; natural products; total synthesis