Tetrahedron
Tetrahedron
5 years ago

Synthesis of a tetracyclic core of Erythrina alkaloids and analogs of crispine A

Synthesis of a tetracyclic core of Erythrina alkaloids and analogs of crispine A
Both enantiomers of C10b methyl analogs of crispine A and a tetracyclic core of Erythrina alkaloids were synthesized starting from l-aspartic acid via a common chiral N-arylethyl succinimide intermediate. The pivotal C10a-C10b bond formation and construction of the C10b stereogenic center were achieved via diastereoselective N-acyliminium ion cyclization. The dibenzylamino group gave stereochemical control where 1,2- and 1,3-stereoinductions led to the cyclized products with opposite configurations at the newly generated stereogenic center. Cope elimination of the dibenzylamino group gave a cyclic enamide which underwent Michael addition and ring closing metathesis of the resulting bis-allyl intermediate in the synthesis of a tetracyclic core of Erythrina alkaloids.

Publisher URL: www.sciencedirect.com/science

DOI: S0040402017306269

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.