title: Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis.
abstract: The total synthesis of 7,10-epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17-C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3-reduction, and a later oxidative synthesis of the THF framework. The C1-C13 and C17-C29 subunits were successfully coupled using a Enders RAMP "linchpin" as the C14-C16 three carbon unit, thereby controlling the chirality at C14 and C16. The labile allyl epoxy moiety was successfully constructed by Grieco-Nishizawa olefination at a final stage of the synthesis.
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
authors: Koji
authors: K
authors: Ochiai
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
authors: Sankar
authors: S
authors: Kuppusamy
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
authors: Yusuke
authors: Y
authors: Yasui
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
authors: Kenji
authors: K
authors: Harada
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan.
authors: Nishant R
authors: NR
authors: Gupta
authors: Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, 060-0812, Japan.
authors: Yohei
authors: Y
authors: Takahashi
authors: Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, 060-0812, Japan.|Showa Pharmaceutical University, 3-3165 Higashi-Tamagawagakuen, Machida, Tokyo, 194-8543, Japan.
authors: Takaaki
authors: T
authors: Kubota
authors: Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, 060-0812, Japan.
authors: Jun'ichi
authors: J
authors: Kobayashi
authors: Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601, Japan. yhayashi@m.tohoku.ac.jp.|Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai, 980-8578, Japan. yhayashi@m.tohoku.ac.jp.
authors: Yujiro
authors: Y
authors: Hayashi
keywords: Enders RMAP; Grieco-Nishizawa olefination; Keck allylation; Shi-epoxidation; total synthesis