Get access

Total Synthesis of (+)-Neopeltolide

Authors

  • Haruhiko Fuwa Dr.,

    1. Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan, Fax: (+81) 22-717-8896
    Search for more papers by this author
  • Shinya Naito,

    1. Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan, Fax: (+81) 22-717-8896
    Search for more papers by this author
  • Tomomi Goto,

    1. Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan, Fax: (+81) 22-717-8896
    Search for more papers by this author
  • Makoto Sasaki Prof. Dr.

    1. Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-amamiya, Aoba-ku, Sendai 981-8555, Japan, Fax: (+81) 22-717-8896
    Search for more papers by this author

  • This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Sports, Culture, Science and Technology (Japan).

Abstract

original image

Rapid elaboration: (+)-Neopeltolide, a novel marine metabolite with potent cytotoxicity against several cancer cell lines, was the target of an efficient total synthesis (see scheme). The construction of the 2,4,6-trisubstituted tetrahydropyran substructure is based on a Suzuki–Miyaura coupling/ring-closing metathesis sequence. BOM=benzyloxymethyl, MPM=4-methoxyphenylmethyl, TIPS=triisopropylsilyl.

Ancillary