3 years ago

Total Synthesis of Dendrochrysanene through a Frame Rearrangement

Total Synthesis of Dendrochrysanene through a Frame Rearrangement
Shumpei Isshiki, Juan Okamura, Naoki Katsuki, Takeo Kawabata, Kouji Kuramochi, Kazunori Tsubaki, Daisuke Fukatsu
The first total synthesis of dendrochrysanene (1) was achieved. The key reaction for the construction of dendrochrysanene was an oxidative frame rearrangement reaction from a phenanthrene dimer to a spiro-lactone skeleton, which we serendipitously identified. Owing to the steric hindrance of the substituent on the peri position of the phenanthrene dimer, high-temperature conditions were required for the rearrangement reaction; however, at such temperatures, the substrate decomposed. To address this issue, we added phenylethylamine or benzylamine to the reaction system. We assumed that the amine trapped generated hydrochloric acid and acted as a ligand for iron, helping to maintain an appropriate redox potential. The total synthesis of dendrochrysanene, involving this rearrangement reaction, is an important sequence interlinking phenanthrene derivatives, phenanthrene dimers, and spiro-lactone compounds, which are frequently isolated from plants of Orchidaceae.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02223

DOI: 10.1021/acs.joc.7b02223

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.