Construction of bicyclo[3.3.1]nonane ring system by means of an intramolecular carbonyl-ene reaction, and its application to the synthesis of related natural products

DOI

Bibliographic Information

Other Title
  • カルボニルーエン反応を鍵反応としたビシクロ[3.3.1]ノナン骨格の構築と天然物合成への応用

Description

(+)-Upial, isolated from the Kaneohe Bay, Oahu sponge Dysidea fragilis, was found to be a nonisoprenoid sesquiterpene aldehyde lactone containing the rare bicyclo[3.3.l]nonane skeleton. Due to its architecturally intriguing structural feature, upial and related analogues have received considerable attention from synthetic chemists over the years. The crucial step for the synthesis of upial lies in the stereocontrolled construction of a bicyclo[3.3.1]nonane ring system with five asymmetric carbon centers as well as facile introduction of the exo-methylene unit. To achieve this crucial step, we planned to exploit an intramolecular carbonyl-ene reaction of a corresponding allylsilane derivative, and we could establish a concise total synthesis of (+)-upial. This synthesis afforded the target compound in 10.2% overall yield in 15 steps from the readily accessible known starting material. Application of the strategy to the synthesis of trifarienols A and B was also investigated.

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Details 詳細情報について

  • CRID
    1390282680612896512
  • NII Article ID
    130006998857
  • DOI
    10.14895/hannou.34.0.137.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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