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Tandem Macrolactone Synthesis: Total Synthesis of (-)-Exiguolide by a Macrocyclization/Transannular Pyran Cyclization Strategy.
Mizukami, Daichi; Iio, Kei; Oda, Mami; Onodera, Yu; Fuwa, Haruhiko.
Afiliação
  • Mizukami D; Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
  • Iio K; Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
  • Oda M; Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
  • Onodera Y; Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai, 981-8577, Japan.
  • Fuwa H; Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo, 112-8551, Japan.
Angew Chem Int Ed Engl ; 61(22): e202202549, 2022 05 23.
Article em En | MEDLINE | ID: mdl-35243740
ABSTRACT
Tetrahydropyran-containing macrolactones were synthesized by integrating Meyer-Schuster rearrangement, macrocyclic ring-closing metathesis, and transannular oxa-Michael addition under gold and ruthenium catalysis. Single-step access to a variety of 14- to 20-membered macrolactones containing a tetrahydropyran ring was possible from readily available linear precursors in good yields and with moderate to excellent diastereoselectivity. A 13-step synthesis of (-)-exiguolide, an anticancer marine macrolide, showcased the feasibility of our tandem reaction sequence for macrolactone synthesis and also demonstrated the power of transannular reactions for rapid assembly of the tetrahydropyran rings of the target natural product.
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Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piranos / Macrolídeos Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Japão

Texto completo: 1 Base de dados: MEDLINE Assunto principal: Piranos / Macrolídeos Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2022 Tipo de documento: Article País de afiliação: Japão