1. A Zincke aldehyde approach to gelsemine
- Author
-
Scott B. Joseph, Christopher D. Vanderwal, and Jonathan K. Lam
- Subjects
Gelsemine ,chemistry.chemical_classification ,Pericyclic reaction ,chemistry.chemical_compound ,Chemistry ,Stereochemistry ,Alkene ,Organic Chemistry ,Drug Discovery ,Total synthesis ,Zincke aldehyde ,Biochemistry - Abstract
We have developed a Zincke-aldehyde-based approach to the complex alkaloid gelsemine. It features a key thermal pericyclic cascade that converts a Zincke aldehyde bearing a pendant alkene into a hydroisoindolone product that shares many structural features with the target molecule. Our efforts to convert these intermediates to gelsemine are also discussed.
- Published
- 2015