Related Experiment Video
Updated: Jun 2, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Novel Entry to the Tricyclic Core of Stemofoline and Didehydrostemofoline
Jochen Dietz1, Stephen F Martin
1Department of Chemistry and Biochemistry, The University of Texas, Austin, TX USA 78712.
Abstract:
A novel approach to the tricyclic core of the Stemona alkaloids stemofoline and didehydrostemofoline has been discovered that features an intramolecular (3+2) dipolar cycloaddition of an unactivated carbon-carbon double bond with an azomethine ylide; the azomethine ylide was generated by an unprecedented reaction that occurred during a Swern oxidation of an α-(N-cyanomethyl)-β-hydroxy ester. In separate experiments, the efficacy of introducing the requisite oxygen functionality at C(8) and the 1-butenyl side chain at C(3) was established.
Related Concept Videos
Direct-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
The direct-acting...
Indirect-Acting Cholinergic Agonists: Chemistry and Structure-Activity Relationship
Reversible inhibitors display short to medium durations of action. Short-acting agents include simple alcohols with...
Stereoisomerism of Cyclic Compounds
Drugs that Stabilize Microtubules
Cholinergic Antagonists: Chemistry and Structure-Activity Relationship
Source And Potency Of Stem Cells

