Total Synthesis of (−)- and ent-(+)-Vindoline
Organic Letters2005Vol. 7(20), pp. 4539–4542
Citations Over TimeTop 10% of 2005 papers
Abstract
[reaction: see text] Two exceptionally concise total syntheses of (-)- and ent-(+)-vindoline are detailed enlisting a diastereoselective tandem [4 + 2]/[3 + 2] cycloaddition of a 1,3,4-oxadiazole. The unique reaction cascade assembles the fully functionalized pentacyclic ring system of vindoline in a single step that forms four C-C bonds and three rings while introducing all requisite functionality and setting all six stereocenters within the central ring including three contiguous and four total quaternary centers.
Related Papers
- → N‐Heterocyclic Carbene Catalyzed Domino Reactions(2011)979 cited
- → Short and Modular Synthesis of Substituted 2-Aminopyrroles(2021)18 cited
- → 6.13 C–C Bond Formation: Cascade or Domino Reaction(2012)7 cited
- → Development of New Synthetic Methods and Their Application to Synthesis of Useful Compounds(2003)6 cited
- → ChemInform Abstract: Four‐ and Sixfold Tandem‐Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches.(2015)