Related Experiment Video
Updated: May 11, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of a leucomitosane via a diastereoselective radical cascade
François Brucelle1, Philippe Renaud
1Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Abstract:
The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of a 3-oxo-leucomitosane related to the mitomycin family of alkaloids.
Related Concept Videos
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Radical Reactivity: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Radical Reactivity: Nucleophilic Radicals

![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)