3 years ago

Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation

Stereochemical Characterization of Polyketide Stereotriads Synthesized via Hydrogen-Mediated Asymmetric syn-Crotylation
Margaret A. Brimble, Jonathan G. Hubert, Daniel P. Furkert, Tilo Söhnel, Mathilde Pantin
The stereoselective access to stereotriads as important polyketide building blocks is reported on the basis of the Krische-type hydrogen-mediated syn-crotylation. The products were obtained with an extremely high diastereoselectivity (dr >99:1), and the newly formed syn stereocenters were controlled solely by the chiral catalyst. The stereochemistry was assigned by crystallography and HPLC for both product manifolds. This extension of the burgeoning transfer hydrogen methodology gives divergent asymmetric access to anti,syn and syn,syn polyketide stereotriads from the same α-chiral starting material and avoids potentially epimerizable aldehyde intermediates.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01820

DOI: 10.1021/acs.joc.7b01820

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.