Related Experiment Video
Updated: May 22, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction
Akio Kamimura1, Koichiro Miyazaki, Shuzo Suzuki
1Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan. ak10@yamaguchi-u.ac.jp
Abstract:
Optically active ent-calystegine B4 was prepared in 13 steps from commercially available chiral L-dimethyl tartrate. The synthesis was achieved by the Michael addition and the aldol reaction of nitromethane to form cycloheptanone in a stereoselective manner. Reduction of the nitro group in the presence of Boc(2)O accomplished an efficient conversion to amino cycloheptanone, which readily afforded the desired ent-calystegine B4.
Related Concept Videos
Conjugate Addition of Enolates: Michael Addition
Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation

