Related Experiment Video
Updated: Sep 14, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Concise synthesis of a lactonamycin model system by diastereoselective dihydroxylation of a highly functionalized
1Department of Chemistry, Columbia University, Havemeyer Hall, New York, New York 10027, USA.
Abstract:
[reaction: see text]. In this Letter, we describe an approach to the highly functionalized tetracycle 6, a model compound corresponding to the CDEF ring system contained in the recently discovered antibiotic lactonamycin. Our approach features an unprecedented, highly stereoselective dihydroxylation of quinone 13a, which leads directly to spirocyclic lactone 15, following acid-promoted deprotection/cyclization. The methodology described herein paves the way for a concise, highly diastereo- and enantioselective synthesis of the natural product.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
07:30A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
Published on: January 21, 2020
Related Concept Videos
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Alkylation of β-Diester Enolates: Malonic Ester Synthesis