Search Results 1-6 of 6

  • Enantioselective Stereodivergent Approach to α-Hydroxy Skipped Dienes: Synthesis of the Western Polyene Fragment of Corallopyronin A

    Nagashima Yoshiyuki , Okada Yuto , Sato Takaaki , Chida Noritaka

    … The α-hydroxy skipped diene structure is stereoselectively synthesized by our method consisting of enantioselective allenylation of an aldehyde, hydroboration of the resulting 1,1-disubstituted allene and Migita-Kosugi-Stille coupling. …

    Chemistry Letters 48(12), 1519-1521, 2019


  • Unified Total Synthesis of Madangamine Alkaloids

    Suto Takahiro , Chida Noritaka , Yanagita Yuta , Nagashima Yoshiyuki , Takikawa Shinsaku , Kurosu Yasuhiro , Matsuo Naoya , Miura Kazuki , Simizu Siro , Sato Takaaki

    … The common intermediate is assembled through <i>N</i>-acyliminium cyclization of a propargylsilane, and formation of the (<i>Z</i>,<i>Z</i>)-skipped diene. … Stereoselective synthesis of the (<i>Z</i>,<i>Z</i>)-skipped diene is especially challenging, and is accomplished by the combination of <i>Z</i>-selective hydroboration of the 1,1-disubstituted allene and subsequent Migita-Kosugi-Stille coupling. …

    Bulletin of the Chemical Society of Japan 92(3), 545-571, 2019


  • Total Syntheses of Madangamine Alkaloids: Development and Application of Syntheses of Skipped Dienes  [in Japanese]

    Sato Takaaki , Suto Takahiro , Yanagita Yuta , Nagashima Yoshiyuki , Matsuo Naoya , Kurosu Yasuhiro , Takikawa Shinsaku , Chida Noritaka

    … A skipped diene is an important functional group widely distributed in biologically active natural products, which possess various types of stereoisomers (Scheme 1A). … Development of an approach to provide all four possible stereoisomers of the skipped diene still remains a major challenge in synthetic organic chemistry. … Herein we report a practical stereodivergent strategy to give an access to the skipped dienes. …

    Symposium on the Chemistry of Natural Products, symposium papers 58(0), Oral23, 2016


  • Total Synthesis of Marine Eicosanoid Hybridalactone  [in Japanese]

    Ota Koichiro , Sugata Naoto , Oshiro Yoshihiko , Kawashima Etsuko , Miyaoka Hiroaki

    … Its unique structure, such as a tetracyclic ring system containing cyclopropane, cyclopentane, 13-membered macrolactone and epoxide, contains seven contiguous stereogenic centers and a skipped <I>Z</I>,<I>Z</I>-configured 1,4-diene motif. …

    Proceedings of the Symposium on Progress in Organic Reactions and Syntheses 37(0), 61-61, 2011


  • New Synthesis of the (3Z,6Z,9S,10R)-Isomers of 9,10-Epoxy-3,6-henicosadiene and 9,10-Epoxy-1,3,6-henicosatriene, Pheromone Components of the Female Fall Webworm Moth, Hyphantria cunea

    NAKANISHI Akira , MORI Kenji

    (3<I>Z</I>,6<I>Z</I>,9<I>S</I>,10<I>R</I>)-9,10-Epoxy-3,6-henicosadiene (1) and (3<I>Z</I>,6<I>Z</I>,9<I>S</I>,10< …

    Bioscience, Biotechnology, and Biochemistry 69(5), 1007-1013, 2005-05-23

    J-STAGE  References (15)

  • 1 Synthetic Study Towards Total Synthesis of Mycothiazole, a Polyketide Thiazole from a Marine Sponge  [in Japanese]

    Sugiyama Hideyuki , Yokokawa Fumiaki , Shioiri Takayuki

    … Furthermore the side chains contain nonconjugated and conjugated diene systems. … According to our synthetic strategy, we started to synthesize the left fragment (3) which contains a thiazole ring and a nonconjugated diene system. … The skipped diene was constructed by using the Stine cross coupling two times. …

    Symposium on the Chemistry of Natural Products, symposium papers 41(0), 1-6, 1999


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