Stereoselective total synthesis of (±)-hyperforin via intramolecular cyclopropanation

Masahiro Uwamori, Masahisa Nakada

研究成果: Article査読

29 被引用数 (Scopus)

抄録

Total synthesis of (±)-hyperforin is described. This total synthesis features an approach via a bicyclo[ 3.3.1]nonane derivative prepared by a three-step sequence: intramolecular cyclopropanation, construction of the C8 all-carbon quaternary stereogenic center, and subsequent regioselective ring opening of cyclopropane. Further steps to obtain (±)-hyperforin include chemo- and stereoselective hydrogenation to generate the C7 stereogenic center, formation of the C9 isopropyl ketone using an organocerium reagent, and cross-metathesis at high temperatures to construct trisubstituted alkenes in side-chains.

本文言語English
ページ(範囲)2022-2025
ページ数4
ジャーナルTetrahedron Letters
54
15
DOI
出版ステータスPublished - 2013 4 10

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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