Related Experiment Video
Updated: Jul 11, 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
Concise, stereoselective approach to the spirooxindole ring system of citrinadin A
Martin Pettersson1, Daniel Knueppel, Stephen F Martin
1Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712, USA.
Abstract:
The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter. The key step involves a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.
More Related Videos
Related Concept Videos
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Stereoisomerism of Cyclic Compounds
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
SN2 Reaction: Stereochemistry
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
Prochirality

