Interesting ChemistryFree EnergyLowest Energy ConformationNatural ProductSimulationChemical Sciences

Chiroptical spectroscopy of the natural product Steganone.

https://doi.org/10.59350/5t09h-k5125
Published in Henry Rzepa's Blog

Steganone is an unusual natural product, known for about 40 years now. The assignment of its absolute configurations makes for an interesting, on occasion rather confusing, and perhaps not entirely atypical story. I will start with the modern accepted stereochemical structure of this molecule, which comes in the form of two separately isolable atropisomers.

References

Organic ChemistryPhysical and Theoretical Chemistry

A Concise Atroposelective Formal Synthesis of (–)‐Steganone

https://doi.org/10.1002/ejoc.201402761
Published in European Journal of Organic Chemistry
Authors Boubacar Yalcouye, Sabine Choppin, Armen Panossian, Frédéric R. Leroux, Françoise Colobert

AbstractWe describe herein the atroposelective formal synthesis of (–)‐steganone, a parent member of Steganotaenia araliacea dibenzocyclooctadiene lignan lactones. Our synthesis features an atropodiastereoselective biaryl Suzuki–Miyaura cross‐coupling reaction with de up to 99 % using as a chiral auxiliary an enantiopure and efficiently converted β‐hydroxy sulfoxide derivative.