3 years ago

General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition

General Approach toward Aspidospermatan-Type Alkaloids Using One-Pot Vilsmeier–Haack Cyclization and Azomethine Ylide Cycloaddition
Guillaume Bélanger, Clémence Hauduc
The development of a new one-pot reaction sequence afforded the tricyclic core of several aspidospermatan-type alkaloids from a linear, densely functionalized substrate. The key sequence features a highly chemoselective formamide activation that triggered a Vilsmeier–Haack cyclization, followed by an azomethine ylide generation and intramolecular cycloaddition. The choice of nucleophile, azomethine ylide precursor, and dipolarophile was crucial to the success of the sequence.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00345

DOI: 10.1021/acs.joc.7b00345

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.