Related Experiment Video
Updated: Oct 21, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Total Syntheses and Biological Evaluation of Lamellolactones A and B via Direct Butenolide Functionalization
Yuto Fuse1, Hwanhee Moon2, Ryuji Kouda1
1Laboratory of Synthetic Natural Products Chemistry and Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo108-8641, Japan.
Abstract:
Lamellolactones A and B are pseudoregioisomeric natural products bearing oxidized butenolide frameworks and have attracted interest in the context of fibrodysplasia ossificans progressiva (FOP). We achieved their first total syntheses via Ni-catalyzed reductive coupling of a common alkyl iodide with α- and β-bromobutenolides. A preliminary examination of alkyl electrophiles indicated that the coupling could be applied to simple primary and secondary alkyl iodides. The route also furnished analogues for comparison of γ-substitution effects on bone morphogenetic protein (BMP)-induced alkaline phosphatase inhibition and cytotoxicity.
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
11:04Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
β-Dicarbonyl Compounds via Crossed Claisen Condensations