Journal of the American Chemical Society
Journal of the American Chemical Society
3 years ago

Total Syntheses of (+)- and (−)-Tetrapetalones A and C

Total Syntheses of (+)- and (−)-Tetrapetalones A and C
Koichi Fujiwara, Travis C. McMahon, Jennifer M. Howell, Jonas F. Buergler, Yutaka Kobayashi, John L. Wood, Matthew W. Haley, Heemal H. Dhanjee
Described herein are syntheses of the naturally occurring polyketides (−)-tetrapetalones A and C and their respective enantiomers. The employed strategy involves initial assembly of a masked N-aryl tetramic acid which is advanced via a highly selective conjugate addition/intramolecular Friedel–Crafts acylation sequence to deliver a key azepine intermediate. Application of recently developed C–H activation chemistry and subsequent Heck cyclization delivers the aglycone framework in an overall 12 steps. Resolution of the aglycone via stereospecific glycosylation with an enantiopure glycosyl donor followed by separation of the derived diastereomers enables further advancement to either (+)- or (−)-tetrapetalones A and C.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b09358

DOI: 10.1021/jacs.7b09358

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.