Asymmetric Total Synthesis of (+)-Mycoepoxydiene: Application of One-Pot Ring-Opening/Cross/Ring-Closing Metathesis

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Other Title
  • 開環／交差／閉環メタセシス反応を利用した(+)-マイコエポキシジエンの全合成

Description

The asymmetric total syntheses of (+)-mycoepoxydiene and (–)-1893A have been completed. The present synthetic strategy features the use of one-pot ring-opening/cross metathesis (ROM/CM) followed by a ring-closing metathesis (RCM) reaction, allowing the concise construction of the 9-oxabicyclo[4.2.1]nona-2,4-diene framework from a 7-oxabicyclo[2.2.1]hept-2-ene derivative and 1,3-butadiene. The sequential metathesis product was converted into (+)-mycoepoxydiene through the oxidative rearrangement of a furfuryl alcohol to a pyranone, thereby establishing its absolute stereochemistry. From the common intermediate, a structurally related natural product (–)-1893A was also synthesized via the vinylogous aldol reaction.

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Details 詳細情報について

  • CRID
    1390282680611095040
  • NII Article ID
    130006996678
  • DOI
    10.14895/hannou.30.0.12.0
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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