A Zincke aldehyde approach to gelsemine. Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Lam, Jonathan K.; Joseph, Scott B.; Vanderwal, Christopher D.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3165
• Page End: 3168
• Publication Date: 2015-06-03
• Subjects: Gelsemine -- Alkaloid -- Total synthesis -- Pericyclic cascade -- Zincke aldehyde; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.089
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: 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.