Related Experiment Video
Updated: Aug 8, 2026

Cellular Lipid Extraction for Targeted Stable Isotope Dilution Liquid Chromatography-Mass Spectrometry Analysis
Published on: November 17, 2011
18-Deoxy-13beta,14-dihydrolycoctam: the lycoctamone rearrangement confirmed
Michael Benn1, Masood Parvez, Oliver Edward Edwards
1Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4.
Abstract:
The structure of the title compound, C23H35NO4, contains a unique pentacyclic ring system wherein one cyclohexyl ring adopts a chair conformation, two cyclohexyl rings are in boat conformations, and a six-membered heterocyclic ring and a cyclopentyl ring are in envelope conformations. The structures of the lycoctamones, alpha,beta-unsaturated aldehydes produced by acid-catalyzed degradation of lactams of lycoctonine-type alkaloids, previously deduced from the results of extensive chemical investigations have been proven to be correct by the determination of the crystal structure of this compound.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
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.

