title: Progress toward the Total Synthesis of Goniodomin A: Stereocontrolled, Convergent Synthesis of the C12-C36 Fragment.
abstract: Goniodomin A is a marine polyether macrolide natural product isolated from the dinoflagellate Alexandrium hiranoi. In this paper, we report stereocontrolled, convergent synthesis of a fully functionalized C12-C36 fragment of goniodomin A. The synthesis of the C12-C25 vinylstannane involved a Wittig reaction and a reductive cycloetherification for the construction of the dihydropyran ring. The C26-C36 thioester was synthesized via a Nozaki-Hiyama-Kishi reaction of an aldehyde and an iodoalkyne, the former of which was easily prepared from (R)-malic acid as a chiral source by taking advantage of substrate-controlled diastereoselective reactions. Finally, a palladium-catalyzed coupling of the C12-C25 vinylstannane and the C26-C36 thioester completed the synthesis of the target compound.
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Seiji
authors.initials: S
authors.lastname: Matsukida
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Taro
authors.initials: T
authors.lastname: Miyoshi
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Kawashima
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Saito
authors.affiliation: Graduate School of Life Sciences, Tohoku University , 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
mesh_terms: D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004987:Ethers; D018942:Macrolides; C059668:goniodomin A; D010165:Palladium